(S)-tert-Butoxycarbonylamino-cyclopropyl-acetic acid

Base Information

• Chemical Name: (S)-tert-Butoxycarbonylamino-cyclopropyl-acetic acid
• CAS No.: 155976-13-9
• Molecular Formula: C10H17NO4
• Molecular Weight: 215.249
• Hs Code.: 29225090
• European Community (EC) Number: 806-492-0
• DSSTox Substance ID: DTXSID10935334
• Nikkaji Number: J1.839.748J
• Mol file: 155976-13-9.mol

Synonyms:Boc-L-Cyclopropylglycine;155976-13-9;(S)-tert-Butoxycarbonylamino-cyclopropyl-acetic acid;(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid;Boc-(S)-cyclopropylglycine;(2S)-2-cyclopropyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;(S)-2-(tert-Butoxycarbonylamino)-2-cyclopropylacetic acid;(S)-BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID;MFCD06659132;(S)-(Boc-amino)-cyclopropylacetic acid;Boc-Gly(cPropyl)-OH;Boc-(S)-2-Cyclopropylglycine;SCHEMBL1273387;DTXSID10935334;QFVJNEASAAJIDF-ZETCQYMHSA-N;Boc-L-cyclopropylglycine, >=95%;CS-D0074;AKOS005264759;Boc-(S)-amino-cyclopropyl-acetic acid;L-Cyclopropylglycine, N-BOC protected;DS-13297;HY-60264;PD196045;B6088;N-(tert-Butoxycarbonyl)-L-cyclopropylglycine;EN300-6472418;N-(tert-Butoxycarbonyl)-2-cyclopropyl-L-glycine;A809705;AS-813/43499841;[(tert-butoxycarbonyl)amino](cyclopropyl)acetic acid;J-009265;2-(tert-butoxycarbonylamino)-2-cyclopropyl-acetic acid;(2S)-[(tert-butoxycarbonyl)amino](cyclopropyl)ethanoic acid;(2S)-2-[(tert-Butoxycarbonyl)amino]-2-cyclopropylethanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-2-cyclopropylacetic acid;{[tert-Butoxy(hydroxy)methylidene]amino}(cyclopropyl)acetic acid;Cyclopropaneacetic acid, alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-, (alphaS)-

Chemical Property of (S)-tert-Butoxycarbonylamino-cyclopropyl-acetic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 79 °C
• Refractive Index: 1.508
• Boiling Point: 364.7 °C at 760 mmHg
• PKA: 3.97±0.10(Predicted)
• Flash Point: 174.4 °C
• PSA: 75.63000
• Density: 1.206 g/cm³
• LogP: 1.76520
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 215.11575802
• Heavy Atom Count: 15
• Complexity: 265

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Boc-2-cyclopropyl-L-glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1CC1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](C1CC1)C(=O)O
• Uses: N-Boc-2-cyclopropyl-L-glycine is a useful synthetic compound.

Technology Process of (S)-tert-Butoxycarbonylamino-cyclopropyl-acetic acid

There total 16 articles about (S)-tert-Butoxycarbonylamino-cyclopropyl-acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

(S)-(1-cyclopropyl-3-phenyl-(E)-allyl)-carbamic acid tert-butyl ester (475586-33-5) → (2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid (155976-13-9)

Guidance literature:

(S)-(1-cyclopropyl-3-phenyl-(E)-allyl)-carbamic acid tert-butyl ester; With ruthenium trichloride; sodium periodate; water; In tetrachloromethane; acetonitrile; at 20 ℃;

With silica gel; dimethyl sulfoxide; In dichloromethane; for 0.5h; Further stages.;

DOI:10.1021/ja027271p

Reference yield: 49.9%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-2-cyclopropylacetic acid (49606-99-7,5687-71-8,15785-26-9,49607-01-4) → (2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid (155976-13-9)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃; for 16h;

Reference yield: 43.0%

methyl 2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate (638207-62-2) → methyl (S)-2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate (936097-43-7) + (2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid (155976-13-9)

Guidance literature:

With dithiothreitol; McIlvaine's buffer cont. EDTA; papain (from Carica papaya); In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 36h; pH=6.2; Enzymatic reaction;

DOI:10.1002/adsc.200606038

upstream raw materials:

(S)-(1-cyclopropyl-3-phenyl-(E)-allyl)-carbamic acid tert-butyl ester

methyl 2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate

cyclopropyl-hydroxyiminoacetic acid

Cyclopropyl methyl ketone

Refernces

• 1、 -. "GRANZYME B DIRECTED IMAGING AND THERAPY". Page/Page column 113. . Retrieved 2019/09/04.
• 2、 Larionov, Oleg V.,De Meijere, Armin. "Practical syntheses of both enantiomers of cyclopropylglycine and of methyl 2-cyclopropyl-2-N-Boc-iminoacetate". . p. 1071 - 1078. Retrieved 2007/10/03.