Hydrochloric Acid → (3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepane-2-thione

HRID 14396Notes

Reaction equation

HRID 14396 reaction equation
Cl.[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C@H:10]1[CH2:16][N:15]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:14](=[S:22])[C@H:13]([NH:23]C(=O)OC(C)(C)C)[CH2:12][CH2:11]1>O1CCOCC1>[NH2:23][C@@H:13]1[CH2:12][CH2:11][C@@H:10]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([F:9])[C:3]=2[F:2])[CH2:16][N:15]([CH2:17][C:18]([F:20])([F:21])[F:19])[C:14]1=[S:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86616756tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]carbamate

Product 1

HCID 86616757(3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepane-2-thione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrochloric acid (4.0 M in dioxane; 3 mL, 12.0 mmol) was added to a solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]carbamate (105 mg, 0.239 mmol) in 1,4-dioxane (3 mL). After 1 h, the reaction was concentrated to give the title compound as a bis hydrochloride salt (96 mg). MS 339.1 (M+1).

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-d1331a2918d1488c9297b55f4c32b83c
Source dataset
uspto-grants-2010_06
Patent number
US07732438B2

Reaction notes

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