Hydrogen Bromide → HCID 88118542, compound

HRID 431838Notes

Reaction equation

HRID 431838 reaction equation
C(OC([N:11]([CH2:21][C@H:22]1[N:26]([C:27]2[N:32]=[CH:31][C:30]([CH2:33][CH2:34][CH3:35])=[CH:29][N:28]=2)[CH2:25][C@H:24]([S:36][C:37](=[O:39])[CH3:38])[CH2:23]1)[CH2:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[F:20])=O)C1C=CC=CC=1.Br>C(O)(=O)C>[F:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[CH2:12][NH:11][CH2:21][C@H:22]1[N:26]([C:27]2[N:32]=[CH:31][C:30]([CH2:33][CH2:34][CH3:35])=[CH:29][N:28]=2)[CH2:25][C@H:24]([S:36][C:37](=[O:39])[CH3:38])[CH2:23]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 91579026HCID 91579026, compound

Product 1

HCID 88118542HCID 88118542, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 137 mg (2.5 mmol) (3R,5S)-Thioacetic acid S-[5-[[benzyloxycarbonyl-(2,5-difluoro-benzyl)-amino]-methyl]-1-(5-propyl-pyrimidin-2-yl)-pyrrolidin-3-yl]ester in 5 ml EE were added 320 μl 33% HBr in acetic acid at 0° C. The solution was stirred at RT for 12 h, poured on NaHCO3 and the inorganic phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and were evaporated. Purification with column chromatography with EtOAc as eluent yielded 65 mg (63%) (3R,5S)-Thioacetic acid S-[5-[(2,5-difluoro-benzylamino)-methyl]-1-(5-propyl-pyrimidin-2-yl)-pyrrolidin-3-yl]ester as colorless oil, MS: 421(MH+). (Nicht in Liste).

Workup

  1. additionpoured on NaHCO3
  2. extractionthe inorganic phase was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customwere evaporated
  6. customPurification with column chromatography with EtOAc as eluent

Sources & evidence

ORD record
ord-0cee083b3f4c4b9bbbb11bd4ee92d65f
Source dataset
uspto-grants-2003_12
Patent number
US06660738B2

Reaction notes

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