L-Proline → 1-(2-(R)-Acetylamino-3-phenyl-propionyl)-pyrrolidin-2-(S)-carboxylic acid (1-amino-isoquinolin-6-ylmethyl)-amide

HRID 1008593Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH:13][C:14]([C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21](=[O:40])[C@H:22]([NH:36][C:37](=[O:39])[CH3:38])[CH2:23][C:24]3[CH:29]=[CH:28][C:27](C4C=CC=CC=4)=[CH:26][CH:25]=3)=[O:15])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.N1CCC[C@H]1C(O)=O>>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH:13][C:14]([C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21](=[O:40])[C@H:22]([NH:36][C:37](=[O:39])[CH3:38])[CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:15])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 145742L-Proline

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

Product 1

HCID 545508931-(2-(R)-Acetylamino-3-phenyl-propionyl)-pyrrolidin-2-(S)-carboxylic acid (1-amino-isoquinolin-6-ylmethyl)-amideYield 839.2%

Procedure

Using the procedure described for example 97f 0.125 g of 1-(2-(R)-acetylamino-3-phenyl)-propionyl)-pyrrolidin-2-(S)-carboxylic acid was converted into 0.90 g (47%) of the title compound. (+)-APCI-MS: 460 (MH+).

Sources & evidence

ORD record: ord-4b3e8e5da2f446f383f54cbaee44a5b1
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797710B2

Reaction notes

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