1-[(S)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid → (2-{2(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(S)-phenyl-ethyl)-carbamic acid methyl ester

HRID 1279112Notes

Reaction equation

HRID 1279112 reaction equation
[CH:1]([O:4][C:5](=[O:36])[NH:6][C@H:7]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15](=[O:29])[NH:16][CH2:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24]([NH2:28])=[N:23][CH:22]=[CH:21]2)=[O:9])(C)C.COC(N[C@@H](C1C=CC=CC=1)C(N1CCC[C@H]1C(O)=O)=O)=O>>[CH3:1][O:4][C:5](=[O:36])[NH:6][C@@H:7]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15](=[O:29])[NH:16][CH2:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24]([NH2:28])=[N:23][CH:22]=[CH:21]2)=[O:9]

Participants

3

Reactant 2

HCID 229584951-[(S)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acidHCID 53885854(2-{2(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(R)-phenyl-ethyl)-carbamic acid isopropyl ester

Product 1

HCID 69781158(2-{2(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(S)-phenyl-ethyl)-carbamic acid methyl esterYield 559.3%

Procedure

Using the procedure described for example 91d 0.110 g of 1-[(S)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid was converted into 0.58 g (36%) of the title compound. (+)-APCI-MS: 462 (MH+).

Sources & evidence

ORD record
ord-9c74d91f4b414041b622679ac8faa511
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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