81872-10-8 Usage
Description
1-Naphthaleneacetic acid is an organic compound that is a derivative of naphthalene, with an acetic acid group attached to the first position of the naphthalene ring. It is a white crystalline solid and is soluble in organic solvents. 1-NAPHTHALENEACETIC ACID has a molecular formula of C12H10O2 and a molecular weight of 190.21 g/mol.
Uses
1-Naphthaleneacetic acid is used as a plant growth regulator in the agricultural industry. It is used to promote root and shoot growth, fruit development, and to control the flowering time in various plants. It is also used to prevent fruit drop and to improve the overall yield and quality of crops.
1-Naphthaleneacetic acid is used as an analytical standard in the chemical industry. It serves as a reference material for the calibration of analytical instruments, such as gas chromatography (GC) or liquid chromatography (LC) mass spectrometry, ensuring accurate and reliable measurements.
1-Naphthaleneacetic acid is used as a chemical intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. Its unique structure and reactivity make it a valuable building block for the development of new and innovative products.
1-Naphthaleneacetic acid is used as a research tool in the field of organic chemistry and biochemistry. It is employed in various studies to investigate the structure, properties, and mechanisms of organic reactions, as well as to explore its potential applications in drug discovery and development.
Originator
Zofenopril Calcium,ZYF Pharm Chemical
Manufacturing Process
9.9 g (0.031 mole) of cis-4-phenylthio-L-proline is suspended in 100 ml of
water (pH 5.6) and the pH is adjusted to 10.2 by the addition of about 20 ml
of 10% sodium bicarbonate to provide a clear solution. The pH is then
adjusted to 9.5 by the addition of about 4.5 ml of concentrated HCl. The
solution is kept at 30°C while 8.1 g (0.033 mole) of (D)-3-(benzoylthio)-2-
methylpropanoic acid chloride in 30 ml of toluene is added simultaneously
with 100 ml of 10% sodium bicarbonate to keep the pH at 9.3. After about
1/4 of the acid chloride is added, a slimy precipitate begins to form which
persists throughout the reaction. After stirring the reaction mixture at pH 9.3
for 2.5 h, it is made strongly acidic by adding 20% HCl in the presence of
ethyl acetate. The aqueous layer is extracted twice with 350 ml portions of
ethyl acetate and the combined organic layers are washed with 300 ml of
saturated brine and dried (MgSO 4 ). The solvent is removed to yield 11.8 g of
foamy solid cis-1-[D-3-(benzoylthyo)-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline hydrochloride.To a solution of this cis-1-[D-3-(benzoylthyo)-2-methyl-1-oxopropyl]-4-
(phenylthio)-L-proline hydrochloride 11.8 g (0.027 mole) in 70 ml of
acetonitrile there is added about 6.0 g of dicyclohexylamine in 25 ml of ether.
A white crystalline precipitate forms immediately. After standing overnight in
the cold room, the solid is filtered and washed with ether to yield (cis)-1-[D-
3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline,
dicyclohexylamine salt (1:1).he slightly moist (cis)-1-[D-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-
(phenylthio)-L-proline dicyclohexylamine salt is stirred for 2.5 h in a mixture
of 300 ml of ethyl acetate and 200 ml of 10% potassium bisulfate. Two clear
layers form. The aqueous layer is extracted with two 200 ml portions of ethyl
acetate and the combined organic layers are dried (MgSO 4 ). The solvent is
removed to yield 10.1 g of foamy solid (cis)-1-[D-3-(benzoylthio)-2-methyl-1-
oxopropyl]-4-(phenylthio)-L-proline; melting point 42-44°C.In practice it is usually used as calcium salt (2:1).
Therapeutic Function
Antihypertensive
Synthesis Reference(s)
The Journal of Organic Chemistry, 33, p. 1675, 1968 DOI: 10.1021/jo01268a091
Check Digit Verification of cas no
The CAS Registry Mumber 81872-10-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,8,7 and 2 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 81872-10:
(7*8)+(6*1)+(5*8)+(4*7)+(3*2)+(2*1)+(1*0)=138
138 % 10 = 8
So 81872-10-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1
81872-10-8Relevant articles and documents
An improved large scale procedure for the preparation of N-Cbz amino acids
Pehere, Ashok D.,Abell, Andrew D.
experimental part, p. 1493 - 1494 (2011/05/16)
A simple and scalable method for the preparation of N-Cbz protected amino acids is presented which uses a mixture of aqueous sodium carbonate and sodium bicarbonate to maintain the appropriate pH during the addition of benzyl chloroformate. The method has been extended to other N-protections and is amenable to large scale preparation of an intermediate toward Zofenopril, an ACE inhibitor.
Process for the preparation of zofenopril calcium salt
-
, (2008/06/13)
A process for the preparation of polymorph A of zofenopril calcium salt in substantially pure form, which comprises: 1) reaction of S(-)-3-benzoylthio-2-methylpropanoic acid chloride with cis-4-phenylthio-L-proline in water at pH ranging from 9.0 to 9.5 and recovery of zofenopril in the acidic form; b) salification of acid zofenopril with a potassium salt in alcoholic solution, and recovery of the resulting potassium salt; c) conversion of the potassium salt to the calcium salt by addition of zofenopril potassium salt aqueous solution to a CaCl2 aqueous solution at a temperature of 70-90° C. with simultaneous seeding to promote the precipitation of polymorph A.
