(S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid
• CAS No.: 51154-06-4
• Molecular Formula: C10H15NO4
• Molecular Weight: 213.233
• Hs Code.: 2933 99 80
• European Community (EC) Number: 637-090-1
• DSSTox Substance ID: DTXSID00350890
• Nikkaji Number: J364.533I
• Wikidata: Q72510128
• Mol file: 51154-06-4.mol

Synonyms:51154-06-4;Boc-3,4-Dehydro-L-proline;(S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid;BOC-3,4-DEHYDRO-PRO-OH;(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-2,5-dihydropyrrole-2-carboxylic acid;MFCD00037896;Boc-deltaPro-OH;Boc-3,4-dehydroPro-OH;N-Boc-L-3,4-dehydroproline;SCHEMBL629585;DTXSID00350890;BMIGSRMSSCUMAZ-ZETCQYMHSA-N;58617-29-1;AKOS015907944;CS-W000410;DS-4250;F10911;A871358;(S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester;(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester

Chemical Property of (S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Chemical Property:

• Melting Point: 92-95oC
• Boiling Point: 336.4 °C at 760 mmHg
• PKA: 3.70±0.20(Predicted)
• Flash Point: 157.3 °C
• PSA: 66.84000
• Density: 1.236 g/cm³
• LogP: 1.18440
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 213.10010796
• Heavy Atom Count: 15
• Complexity: 303

Purity/Quality:

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

Boc-3,4-dehydro-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 36-50
• Safety Statements: 26-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC=CC1C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC=C[C@H]1C(=O)O
• Uses: Boc-3,4-Dehydro-L-Proline is an N-terminal protected 3,4-Dehydro-L-proline. It is used in solid-phase peptide synthesis (SPPS) to make peptides. 3,4-Dehydro-L-proline is a alternate substrate of the amino acid oxidase, NikD.

Technology Process of (S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

There total 5 articles about (S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic 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: 76.0%

N-tert-Butyloxycarbonyl-3,4-dehydro-DL-prolin (51077-13-5) → N-tert-Butyloxycarbonyl-L-prolin (51077-13-5,51154-06-4,58617-29-1)

Guidance literature:

With (R)-2-methyl-p-nitrobenzylamine;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester (51154-06-4)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap; triethylamine / dichloromethane / 19 h / 0 - 20 °C

2: dmap; triethylamine / dichloromethane / 5 h / 0 - 20 °C

3: sodium tetrahydroborate / tert-butyl alcohol / 80 °C

4: pyridine; dihydrogen peroxide / water; dichloromethane / 3 h / 20 °C

5: lithium hydroxide / tetrahydrofuran; water / 2 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; dihydrogen peroxide; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/acs.orglett.7b03525

Reference yield:

N-BOC-3,4-didehydro-(S)-proline methyl ester (74844-93-2) + (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate (83548-46-3) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4) → 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid (90104-21-5) + (S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester (51154-06-4) + (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-13-1)

Guidance literature:

N-BOC-3,4-didehydro-(S)-proline methyl ester; (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate; 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With sodium hydroxide; water; at 40 ℃; for 2h;

With hydrogenchloride; In water; at 5 ℃; pH=5;

With hydrogenchloride; sodium hydroxide; sodium hypochlorite; more than 3 stages; Product distribution / selectivity;

upstream raw materials:

N-BOC-3,4-didehydro-(S)-proline methyl ester

(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

3,4-dehydro-1-(9-fluorenylmethoxycarbonyl)-L-proline

C₁₈H₂₁N₃O₃

(S)-2-benzyl 1-tert-butyl 1H-pyrrole-1,2(2H,5H)-dicarboxylate

N-Tosyl-3,4-epoxy-L-prolin-methylester

Refernces

• 1、 -. "METHOD FOR PRODUCING FLUORINATED PROLINE DERIVATIVE". Page/Page column 38-40. . Retrieved 2008/06/13.