3-[(7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid tert-butyl ester → 3-[(7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid

HRID 1481210Notes

Reaction equation

HRID 1481210 reaction equation
C([O:5][C:6](=[O:34])[C:7]([CH3:33])([CH3:32])[CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]([C:30]#[N:31])[C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[C:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:16]=2)=[O:11])(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH2:23]([C:17]1[CH:16]=[C:15]2[C:20]([C:21]([OH:22])=[C:12]([C:10]([NH:9][CH2:8][C:7]([CH3:32])([CH3:33])[C:6]([OH:34])=[O:5])=[O:11])[N:13]=[C:14]2[C:30]#[N:31])=[CH:19][CH:18]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 898128923-[(7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid tert-butyl ester

Product 1

HCID 717364353-[(7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acidYield 64.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 3-[(7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid tert-butyl ester (22 mg, 0.05 mmole) in a mixture of trifluoroacetic acid (3 ml) and dichloromethane (1 ml) was stirred room temperature for 80 minutes before it was concentrated to give the title compound as a white solid (13 mg). LC-MS ESI−: 402 (M−1)−.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-38ac717f4e59470f97df9bd77077a546
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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