Hydrochloric Acid → HCID 24765378, compound

HRID 1987592Notes

Reaction equation

HRID 1987592 reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[C@@H:7]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:8]([CH3:13])[C:9]([F:12])([F:11])[F:10])C.Cl>C1COCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([NH:14][C@H:7]([CH2:6][OH:5])[C@@H:8]([CH3:13])[C:9]([F:10])([F:11])[F:12])(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 68833307HCID 68833307, compound

Product 1

HCID 24765378HCID 24765378, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium borohydride (2.0 M in THF, 0.34 mL) was added to a solution of (2S,3S)-2-(4-chloro-benzenesulfonylamino)-4,4,4-trifluoro-3-methyl-butyric acid ethyl ester (126 mg, 0.34 mmol) in THF (5 mL) and stirred for 12 h. Careful addition of 2N HCl (aq) was performed until pH<2. Organic solvent was removed in vacuo. The aqueous layer was extracted with EtOAc (2×20 mL) and organic layers were combined and washed with brine. The organic layer was dried over Na2SO4 and solvent removed in vacuo. The crude solid was purified by flash chromatography (20% EtOAc/hexanes) to provide a white solid (80 mg) in 71 % yield. Mass Spectrum (−ESI): 330.0 [M−H]−.

Workup

  1. customOrganic solvent was removed in vacuo
  2. extractionThe aqueous layer was extracted with EtOAc (2×20 mL) and organic layers
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4 and solvent
  5. customremoved in vacuo
  6. customThe crude solid was purified by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0eb29a96498c407f88be342289a208e1
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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