Trans Methyl O-benzyl-L-4-hydroxyproline

Base Information

• Chemical Name: Trans Methyl O-benzyl-L-4-hydroxyproline
• CAS No.: 113490-76-9
• Molecular Formula: C13H17 N O3
• Molecular Weight: 235.283
• DSSTox Substance ID: DTXSID50428634
• Nikkaji Number: J1.653.947C
• Wikidata: Q82241448
• Mol file: 113490-76-9.mol

Synonyms:113490-76-9;Trans Methyl O-benzyl-L-4-hydroxyproline;(2S,4R)-4-Benzyloxy-pyrrolidine-2-carboxylic acid methyl ester;Methyl (2S,4R)-4-phenylmethoxypyrrolidine-2-carboxylate;(4R)-4-Benzyloxy-L-Proline methyl ester;(2S,4R)-METHYL 4-(BENZYLOXY)PYRROLIDINE-2-CARBOXYLATE;METHYL (2S,4R)-4-(BENZYLOXY)PYRROLIDINE-2-CARBOXYLATE;trans-Methyl 4-(benzyloxy)pyrrolidine-2-carboxylate;methyl (2S,4R)-4-benzyloxypyrrolidine-2-carboxylate;4-Benzyloxy-pyrrolidine-2-carboxylic acid methyl ester;SCHEMBL15099494;DTXSID50428634;MFCD09878836;4beta-(Benzyloxy)-L-proline methyl ester;PS-20008;CS-0099757;Methyl2,3-O-isopropylidene-5-O-benzyl-?-D-ribofuranoside

Chemical Property of Trans Methyl O-benzyl-L-4-hydroxyproline

Chemical Property:

• Vapor Pressure: 0.000154mmHg at 25°C
• Melting Point: 124-125 °C
• Refractive Index: 1.54
• Boiling Point: 331.6°Cat760mmHg
• PKA: 7.23±0.10(Predicted)
• Flash Point: 154.3°C
• PSA: 47.56000
• Density: 1.14g/cm³
• LogP: 1.43550
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 235.12084340
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

98%min ^*data from raw suppliers

trans-Methyl4-(benzyloxy)pyrrolidine-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(CN1)OCC2=CC=CC=C2
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H](CN1)OCC2=CC=CC=C2

Technology Process of Trans Methyl O-benzyl-L-4-hydroxyproline

There total 7 articles about Trans Methyl O-benzyl-L-4-hydroxyproline 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: 67.0%

1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (136024-60-7) → 4(R)-(phenylmethoxy)-(S)-proline methyl ester (113490-76-9)

Guidance literature:

1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate; With trifluoroacetic acid; In dichloromethane; at 20 - 35 ℃; for 5h;

With sodium hydrogencarbonate; In water; pH=8;

Reference yield: 48.0%

methanol (67-56-1) + (2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (40350-83-2,54631-82-2,54631-81-1) → 4(R)-(phenylmethoxy)-(S)-proline methyl ester (113490-76-9)

Guidance literature:

With thionyl chloride; for 18h; Ambient temperature;

DOI:10.1021/jm00399a033

Reference yield:

benzyl bromide (100-39-0) → 4(R)-(phenylmethoxy)-(S)-proline methyl ester (113490-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.21 g / NaH / tetrahydrofuran / 5 h / Heating

2: 48 percent / SOCl₂ / 18 h / Ambient temperature

With thionyl chloride; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jm00399a033

upstream raw materials:

methanol

(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

benzyl bromide

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Downstream raw materials:

(2S,4R)-4-(benzyloxy)-1-(2,2-diphenylacetyl)pyrrolidine-2-carboxylic acid

C₂₇H₂₇NO₄

(S)-2-[((2S,4R)-4-Benzyloxy-1-{(2S,3R)-3-benzyloxy-2-[(S)-5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-butyryl}-pyrrolidine-2-carbonyl)-amino]-4-(4-benzyloxy-phenyl)-butyric acid methyl ester

(S)-2-({(2S,4R)-1-[(2S,3R)-2-((S)-2-Amino-5-benzyloxycarbonylamino-pentanoylamino)-3-benzyloxy-butyryl]-4-benzyloxy-pyrrolidine-2-carbonyl}-amino)-4-(4-benzyloxy-phenyl)-butyric acid methyl ester

Refernces

• 1、 -. "HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE". . . Retrieved 2013/07/19.