(S)-3-((S)-1-Cyclopentyloxycarbonyl-3-methyl-butylcarbamoyl)-7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester → (S)-7-Amino-3-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 2276994Notes

Reaction equation

HRID 2276994 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18](=[O:33])[NH:19][C@H:20]([C:25]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:34]([O-])=O)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd].[C]>[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18](=[O:33])[NH:19][C@H:20]([C:25]([O:27][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH2:34])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 57971746(S)-3-((S)-1-Cyclopentyloxycarbonyl-3-methyl-butylcarbamoyl)-7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 67052676(S)-7-Amino-3-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-((S)-1-Cyclopentyloxycarbonyl-3-methyl-butylcarbamoyl)-7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (3.14 g, 6.24 mmol) and Pd/carbon (0.4 g) were suspended in EtOAc (20 ml). The reaction was stirred under a hydrogen atmosphere (balloon pressure) for 16 h. The solution was filtered through a pad of celite and the solvent removed. The crude product (3.04 g) was used in the next step without further purification. LCMS purity 83%, m/z 474 [M++H]+

Workup

  1. filtrationThe solution was filtered through a pad of celite
  2. customthe solvent removed
  3. customThe crude product (3.04 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-b894ebc0e1b74267b76adcbe59d99b1c
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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