Methyl (R)-(+)-2-isocyanato-3-phenylpropionate → (R)-2-(4-Phenethyloxybenzyloxycarbonylamino)-3-phenyl-propionic Acid Methyl Ester

HRID 2120578Notes

Reaction equation

HRID 2120578 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:18][O:19][C:20](=[O:32])[C@H:21]([N:29]=[C:30]=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C1C=CN=CC=1)C>[CH3:18][O:19][C:20](=[O:32])[C@H:21]([NH:29][C:30]([O:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:15][CH:14]=1)=[O:31])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6558897Methyl (R)-(+)-2-isocyanato-3-phenylpropionateHCID 12990905(4-Phenethyloxyphenyl)methanol

Product 1

HCID 12990906(R)-2-(4-Phenethyloxybenzyloxycarbonylamino)-3-phenyl-propionic Acid Methyl EsterYield 96.9%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

(4-Phenethyloxyphenyl)methanol 11(1.141 g, 5.0 mmol), (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5 (1.036 g, 5.0 mmol) and DMAP (10 mg) were combined and heated until molten and stirred for 20 min. Upon cooling the residue was purified by chromatography to give about 2.1 g of (R)-2-(4-phenethyloxybenzyloxycarbonylamino)-3-phenyl-propionic acid methyl ester 12.

Workup

  1. temperatureheated
  2. temperatureUpon cooling the residue
  3. customwas purified by chromatography

Sources & evidence

ORD record
ord-ab890d7138c04afca959e42164198411
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

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