Ammonium Chloride → HCID 86712809, compound

HRID 876377Notes

Reaction equation

HRID 876377 reaction equation
C([O:3][C:4](=O)[C:5]([F:24])([F:23])[C@@:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])([NH:9][S@@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[CH2:7][F:8])C.[Cl-].[NH4+]>O1CCCC1.[BH4-].[Li+]>[F:24][C:5]([F:23])([CH2:4][OH:3])[C@@:6]([NH:9][S:10]([C:12]([CH3:13])([CH3:14])[CH3:15])=[O:11])([CH2:7][F:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 71092981HCID 71092981, compound

Product 1

HCID 86712809HCID 86712809, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 4148881Lithium borohydrideSolvent

Procedure

(S)-2,2,4-trifluoro-3-(2-fluoro-phenyl)-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester (intermediate F3.1) (177 mg, 461 μmol) was dissolved in tetrahydrofuran (4 ml) and at 0° C. lithium borohydride (2 M solution in tetrahydrofuran; (461 μl, 921 μmol) was added dropwise. After 30 minutes the reaction was complete. For the workup, the reaction mixture was poured into a mixture of ice water and a saturated solution of ammonium chloride. Thereafter, the mixture was extracted with ethyl acetate (3×), the organic layers were combined, washed with brine, dried over sodium sulphate and evaporated at reduced pressure. The resulting product was pure enough to be engaged in the next step without further purification. The 2-methyl-propane-2-sulfinic acid [(S)-2,2-difluoro-1-fluoromethyl-1-(2-fluoro-phenyl)-3-hydroxy-propyl]-amide (153 mg, 97% yield) was obtained as a white foam. MS (ISN): m/z=342.2 [M+H]+.

Workup

  1. addition(461 μl, 921 μmol) was added dropwise
  2. extractionThereafter, the mixture was extracted with ethyl acetate (3×)
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated at reduced pressure
  6. customto be engaged in the next step without further purification

Sources & evidence

ORD record
ord-1a86b0a6ce2d4d9b9055b459de463739
Source dataset
uspto-grants-2015_03
Patent number
US08987255B2

Reaction notes

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