Sodium Bicarbonate → HCID 10201004, compound

HRID 458392Notes

Reaction equation

HRID 458392 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][C:14](=[O:16])[CH3:15])[CH2:10][C@H:9]1[CH2:17][N:18](C(OCC1C=CC=CC=1)=O)[CH2:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[F:27])=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])(O)=O.[Na+]>Br.C(O)(=O)C.CCOCC>[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][C:14](=[O:16])[CH3:15])[CH2:10][C@H:9]1[CH2:17][NH:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[F:27])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86584862HCID 86584862, compound

Product 1

HCID 10201004HCID 10201004, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

50 mg (0.09 mmol) (2S,4R)-4-acetylsulfanyl-2-{[benzyloxycarbonyl-(2,5-difluoro-benzyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid butyl ester were dissolved in 130 μl 33% HBr in acetic acid and stirred at 0° C. for 30 min, and at RT for 1 h. The solution was diluted with ether and poured on saturated NaHCO3 solution, carefully. The inorganic layer was extracted with EtOAc, the combined organic phases were washed with water and brine, dried over Na2SO4 and evaporated. Column chromatography yielded 13 mg (35%) (2S,4R)-4-acetylsulfanyl-2-[(2,5-difluoro-benzylamino)-methyl]-pyrrolidine-1-carboxylic acid butyl ester as colorless oil, MS: 401 (MH+).

Workup

  1. waitat RT for 1 h
  2. extractionThe inorganic layer was extracted with EtOAc
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-cdb46de90c724ea5a611d000af9f3c8e
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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