Trifluoroacetic acid → HCID 86670225, compound

HRID 2178201Notes

Reaction equation

HRID 2178201 reaction equation
[C:1]([CH2:3][S:4][C@H:5]1[CH2:9][O:8][CH2:7][C@@H:6]1[C@:10]([N:19](CC1C=CC(OC)=CC=1OC)[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[CH3:11])#[N:2].FC(F)(F)C(O)=O>>[C:1]([CH2:3][S:4][C@H:5]1[CH2:9][O:8][CH2:7][C@@H:6]1[C@:10]([NH:19][C:20](=[O:25])[C:21]([F:22])([F:24])[F:23])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[CH3:11])#[N:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86670224HCID 86670224, compound

Product 1

HCID 86670225HCID 86670225, compound

Procedure

A solution of N-[rel-(S)-1-((3S,4R)-4-cyanomethylsulfanyl-tetrahydro-furan-3-yl)-1-(2-fluoro-phenyl)-ethyl]-N-(2,4-dimethoxy-benzyl)-2,2,2-trifluoro-acetamide (1.65 g, 3.13 mmol) in trifluoroacetic acid (14.5 ml, 188 mmol) was stirred at room temperature overnight. The reaction mixture was extracted with a mixture of a saturated solution of sodium hydrogencarbonate and ethyl acetate/tetrahydrofuran. The combined organic layers were dried over sodium sulphate and evaporated at reduced pressure. The crude N-[rel-(S)-1-((3S,4R)-4-cyanomethylsulfanyl-tetrahydro-furan-3-yl)-1-(2-fluoro-phenyl)-ethyl]-2,2,2-trifluoro-acetamide was obtained as a white solid and engaged in the following step without further purification. MS (ISP): m/z=375.3 [M+H]+.

Workup

  1. extractionThe reaction mixture was extracted with a mixture of a saturated solution of sodium hydrogencarbonate and ethyl acetate/tetrahydrofuran
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-bda129f9e9174eb7acb57dd6a0784923
Source dataset
uspto-grants-2015_06
Patent number
US09067924B2

Reaction notes

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