HCID 57445163, compound → HCID 68618135, compound

HRID 1893659Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:10]([N:12]1[CH2:16][CH:15]([O:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]=2)[CH2:14][CH:13]1[C:30]([OH:32])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][O:38][C:39]([C:41]1([NH2:47])[CH2:43][CH:42]1[CH2:44][C:45]#[N:46])=[O:40]>>[CH3:37][O:38][C:39]([C:41]1([NH:47][C:30]([CH:13]2[CH2:14][CH:15]([O:17][C:18]3[C:27]4[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=4)[CH:21]=[CH:20][N:19]=3)[CH2:16][N:12]2[C:10](=[O:11])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:33]([CH3:35])([CH3:34])[CH3:36])=[O:32])[CH2:43][CH:42]1[CH2:44][C:45]#[N:46])=[O:40]

Participants

Reactant 2

HCID 57445163HCID 57445163, compound

HCID 68617089HCID 68617089, compound

Product 1

HCID 68618135HCID 68618135, compound

Procedure

1-{[1-(2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-cyanomethyl-cyclopropanecarboxylic acid methyl ester was prepared according to the method presented in the synthesis of compound 31. Treatment of 1-(2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-2-carboxylic acid (387 mg, 0.69 mmol) and 1-amino-2-cyanomethyl-cyclopropanecarboxylic acid methyl ester occurred under the same conditions, adjusted for scale, to afford the desired methyl ester (349 mg, 74%). LCMS found 638.0 [M+H]+.

Sources & evidence

ORD record: ord-1e79bc1b890945aa9e317f9734932560
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513186B2

Reaction notes

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