HCID 86731203, compound → HCID 86731202, compound

HRID 2277147Notes

Reaction equation

HRID 2277147 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:35]=[CH:34][C:9]([C:10]([NH:12][C:13]3[CH:14]=[C:15]([CH:28]=[CH:29][C:30]=3[N+:31]([O-])=O)[O:16][CH2:17][C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1>[C].[Pd].C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:35]=[CH:34][C:9]([C:10]3[NH:12][C:13]4[CH:14]=[C:15]([O:16][CH2:17][C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])[CH:28]=[CH:29][C:30]=4[N:31]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86731203HCID 86731203, compound

Product 1

HCID 86731202HCID 86731202, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl ((2S)-1-(3-((4-(cyclopropylmethoxy)benzoyl)amino)-4-nitrophenoxy)propan-2-yl)carbamate (1.00 g), 10% palladium-carbon (containing water (50%), 1.00 g) and THF (10 mL) was stirred at room temperature for 30 min under a hydrogen atmosphere. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. A solution of the obtained solid in acetic acid (20 mL) was stirred at 80° C. for 1 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (901 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. stirringA solution of the obtained solid in acetic acid (20 mL) was stirred at 80° C. for 1 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1ac9517231c84783a7ea31f669f86a6a
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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