Ammonia → (R)-2-[(R)-2-(5-bromo-2-fluoro-phenyl)-2-(2-nitro-benzenesulfonylamino)propoxy]-3,3,3-trifluoro-2-methyl-propionamide

HRID 39235Notes

Reaction equation

HRID 39235 reaction equation
C(O[C:4](=[O:36])[C@:5]([O:11][CH2:12][C@@:13]([C:28]1[CH:33]=[C:32]([Br:34])[CH:31]=[CH:30][C:29]=1[F:35])([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[CH3:14])([CH3:10])[C:6]([F:9])([F:8])[F:7])C.[NH3:37]>CO>[Br:34][C:32]1[CH:31]=[CH:30][C:29]([F:35])=[C:28]([C@:13]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])(=[O:17])=[O:18])([CH3:14])[CH2:12][O:11][C@@:5]([CH3:10])([C:6]([F:8])([F:7])[F:9])[C:4]([NH2:37])=[O:36])[CH:33]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66666252(R)-2-[(R)-2-(5-bromo-2-fluoro-phenyl)-2-(2-nitro-benzenesulfonylamino)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid ethyl ester

Product 1

HCID 66665884(R)-2-[(R)-2-(5-bromo-2-fluoro-phenyl)-2-(2-nitro-benzenesulfonylamino)propoxy]-3,3,3-trifluoro-2-methyl-propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-2-[(R)-2-(5-bromo-2-fluoro-phenyl)-2-(2-nitro-benzenesulfonylamino)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid ethyl ester (26.6 g, 44.2 mmol) in 7N NH3 in MeOH (75 ml) was stirred for 16 h at 50° C. The solvent was removed under reduced pressure and the residual solid re-crystallized from Et2O to give the title compound as yellow crystals: TLC (hexane-EtOAc 1:1): Rf=0.35; UPLC RtH5=1.184 min; ESIMS: 589, 591 [(M+NH4)+]; 1H NMR (360 MHz, CDCl3): δ 7.85 (d, 1H), 7.64 (m, 3H), 7.44 (d, 1H), 7.41 (dd, 1H), 7.26 (m, 1H), 6.68 (br s, 1H), 6.57 (dd, 1H), 6.19 (s, 1H), 5.54 (br s, 1H), 4.24 (d, 1H), 3.93 (d, 1H), 1.79 (s, 3H), 1.67 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residual solid re-crystallized from Et2O

Sources & evidence

ORD record
ord-ac71865d929949448b83eae7a2ffa29f
Source dataset
uspto-grants-2013_09
Patent number
US08524897B2

Reaction notes

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