1-(2-(R)-ethoxycarbonylamino-3-(4-methoxyphenyl)-propionyl)-pyrrolidin-2-(S)-carboxylic acid → (2-{2-(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin 1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl)-carbamic acid ethyl ester

HRID 1008573Notes

Reaction equation

HRID 1008573 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH:13]C([C@@H]3CCCN3C(=O)[C@H](NC(=O)C)CC3C=CC(C4C=CC=CC=4)=CC=3)=O)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:41]([O:43][C:44]([NH:46][C@H:47]([CH2:58][C:59]1[CH:64]=[CH:63][C:62]([O:65][CH3:66])=[CH:61][CH:60]=1)[C:48]([N:50]1[CH2:54][CH2:53][CH2:52][C@H:51]1[C:55]([OH:57])=O)=[O:49])=[O:45])[CH3:42]>>[CH2:41]([O:43][C:44](=[O:45])[NH:46][C@H:47]([CH2:58][C:59]1[CH:60]=[CH:61][C:62]([O:65][CH3:66])=[CH:63][CH:64]=1)[C:48]([N:50]1[CH2:54][CH2:53][CH2:52][C@H:51]1[C:55](=[O:57])[NH:13][CH2:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([NH2:1])=[N:3][CH:4]=[CH:5]2)=[O:49])[CH3:42]

Participants

3

Reactant 2

HCID 229584401-(2-(R)-ethoxycarbonylamino-3-(4-methoxyphenyl)-propionyl)-pyrrolidin-2-(S)-carboxylic acidHCID 865886941-(2-(R)-Acetylamino-3-biphenyl-4yl-propionyl)-pyrrolidin-2-(S)-carboxylic acid (1-amino-isoquinolin-6-ylmethyl)-amide

Product 1

HCID 69780696(2-{2-(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin 1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl)-carbamic acid ethyl esterYield 79%

Procedure

Using the procedure described in example 97f 0.115 g of 1-(2-(R)-ethoxycarbonylamino-3-(4-methoxyphenyl)-propionyl)-pyrrolidin-2-(S)-carboxylic acid was converted into 0.130 g (79%) of the title compound. (+)-APCI-MS: 520 (MH+).

Sources & evidence

ORD record
ord-0a99bc1ea314440e85082dc190b19032
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

Loading…