Trifluoroacetic acid → (4S,7S,10aS)-4-amino-7-vinylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one trifluoroacetate

HRID 529555Notes

Reaction equation

HRID 529555 reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9]C(=O)OC(C)(C)C)[CH2:7][CH2:6][S:5][C@H:4]2[CH2:17][CH2:18][CH2:19][C@@H:20]([CH:21]=[CH2:22])[N:3]12.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24]>C(Cl)Cl>[F:26][C:25]([F:28])([F:27])[C:23]([OH:29])=[O:24].[NH2:9][C@H:8]1[CH2:7][CH2:6][S:5][C@H:4]2[CH2:17][CH2:18][CH2:19][C@@H:20]([CH:21]=[CH2:22])[N:3]2[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86706232tert-butyl (4S,7S,10aS)-5-oxo-7-vinyloctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Product 1

HCID 86706233(4S,7S,10aS)-4-amino-7-vinylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one trifluoroacetateYield 103.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4S,7S,10aS)-5-oxo-7-vinyloctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (44 mg, 0.13 mmol) in DCM (1 mL) was added TFA (1.0 mL, 13 mmol). The reaction was stirred at rt for 1 hr. The reaction mixture was concentrated and dried under high vacuum to afford (4S,7S,10aS)-4-amino-7-vinylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one trifluoroacetate (46 mg, 0.134 mmol, 100% yield) as an oil. Anal. Calcd. for C11H18N2OS m/z 226.3. found: 227.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-76bad17b5b98463f85a1643a8e9b574c
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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