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

HRID 2304324Notes

Reaction equation

HRID 2304324 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)[CH3:2].C(OC(N[C@H](C1CCCCC1)C(N1CCC[C@H]1C(O)=O)=O)=O)C>>[CH2:1]([O:4][C:5](=[O:36])[NH:6][C@H:7]([CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]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])[CH3:2]

Participants

3

Reactant 2

HCID 229584861-[(R)-ethoxycarbonylamino-cyclohexyl-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 69780080(2-{2-(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-1-(R)-cyclohexyl-2-oxo-ethyl)-carbamic acid ethyl esterYield 124.9%

Procedure

Using the procedure described in example 91d 0.350 g of 1-[(R)-ethoxycarbonylamino-cyclohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid was converted into 0.430 g (83%) of the title compound. (+)-APCI-MS: 482 (MH+).

Sources & evidence

ORD record
ord-9e93651e4dd44cc99dc7ef5d2b787d1d
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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