Proline benzyl ester hydrochloride → (N-tert.-Butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester

HRID 1279121Notes

Reaction equation

HRID 1279121 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:23]([O:30][C:31](=[O:37])[C@@H:32]1[CH2:36][CH2:35][CH2:34][NH:33]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([O:30][C:31]([C@@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:37])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 2733413Proline benzyl ester hydrochlorideHCID 7017908Boc-O-methyl-D-tyrosine

Product 1

HCID 69780134(N-tert.-Butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionyl]-pyrrolidine-2-(S)-carboxylic acid benzyl esterYield 52.5%

Procedure

Reaction of 3.5 g of N-tert.-Butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid and 2.9 g of (L)-proline benzyl ester hydrochloride according to the procedure described for example 91b gave 3.0 g (52%) of the title compound as a yellow oil. (+)-APCI-MS: 505 (MNa+).

Sources & evidence

ORD record
ord-0af4dfd0302f49938e50f14db938a5f2
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

Loading…