Ammonia → methyl N-{[3'-(aminomethyl)biphenyl-4-yl]sulfonyl}valinate

HRID 606509Notes

Reaction equation

HRID 606509 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@H:19]([C:23]([O:25][CH3:26])=[O:24])[CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].N.CO>C1COCC1.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][C@H:19]([C:23]([O:25][CH3:26])=[O:24])[CH:20]([CH3:21])[CH3:22])(=[O:17])=[O:16])=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 66769160methyl N-[(3'-cyanobiphenyl-4-yl)sulfonyl]valinate

Product 1

HCID 66769176methyl N-{[3'-(aminomethyl)biphenyl-4-yl]sulfonyl}valinateYield 76%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl N-[(3′-cyanobiphenyl-4-yl)sulfonyl]valinate obtained in Reference Example 93 (5.00 g, 13.4 mmol), Raney-nickel (5.00 g) and 28% aqueous ammonia (50 mL) in THF (50 ml)-methanol (50 mL) was stirred at room temperature for 15 hr under hydrogen atmosphere (1 atm). The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. A mixed solvent of ethyl acetate-hexane was added to the residue, and the precipitated insoluble material was filtered off. The filtrate was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and diethyl ether was added to the residue. The precipitated solid was collected by filtration to give the title compound as a white powder (3.84 g, 76%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionA mixed solvent of ethyl acetate-hexane was added to the residue
  4. filtrationthe precipitated insoluble material was filtered off
  5. washThe filtrate was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure, and diethyl ether
  8. additionwas added to the residue
  9. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-0aec9decdc4540d6b8cd8466e00d937a
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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