Ethyl acetate hexane → 4-(1-Hydroxyamino-isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 251804Notes

Reaction equation

HRID 251804 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[C:19]3[CH:20]=[CH:21][N:22]=[C:23]([N+:28]([O-])=[O:29])[C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O.CCCCCC>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[C:19]3[CH:20]=[CH:21][N:22]=[C:23]([NH:28][OH:29])[C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:16])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 668684924-(1-Nitro-isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 871841344-(1-Hydroxyamino-isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the nitro-isoquinoline from step B (0.81 mmol, 1.86 mmol) and Pd/C (10%, 0.081 g) in methanol (50 mL) was stirred under hydrogen overnight, filtered and evaporated to give a crude oil. Chromatography on silica eluting with a gradient of 20% to 70% of EtOAc/Hexane gave an oil. (0.43 g, 55%). LCMS (+APCI) m/z 423 (M+H).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customto give a crude oil

Sources & evidence

ORD record
ord-a7963eda582442669dcd546ab34ab16a
Source dataset
uspto-grants-2011_01
Patent number
US07867999B1

Reaction notes

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