Hydrochloric Acid → HCID 67176856, compound

HRID 885213Notes

Reaction equation

HRID 885213 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>C(O)C>[NH2:8][C@@H:12]([CH2:13][CH2:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)(=[O:17])=[O:16])[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67177216HCID 67177216, compound

Product 1

HCID 67176856HCID 67176856, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (S)-4-[2-(4-fluoro-phenylsulfonyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.21 g) was added under an argon atmosphere 5.5 M HCl solution in ethanol (2 ml). The mixture was stirred for 4 h. The mixture was concentrated. The residue was dissolved in dichloromethane and an excess of ammonia in methanol and some silica gel was added. The solvents were evaporated and the crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/methanol=90:10) to give (S)-2-amino-4-(4-fluoro-phenylsulfonyl)-butan-1-ol (0.10 g) as a colourless oil. MS (ISP): 248.1 ([M+H]+).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. additionan excess of ammonia in methanol and some silica gel was added
  4. customThe solvents were evaporated
  5. customthe crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/methanol=90:10)

Sources & evidence

ORD record
ord-301bda0b0f0c4eb08034a1453921201f
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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