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

HRID 529557Notes

Reaction equation

HRID 529557 reaction equation
[CH2:1]([C@H:3]1[N:13]2[C@@H:7]([S:8][CH2:9][CH2:10][C@H:11]([NH:15]C(=O)OC(C)(C)C)[C:12]2=[O:14])[CH2:6][CH2:5][CH2:4]1)[CH3:2].[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].[NH2:15][C@H:11]1[CH2:10][CH2:9][S:8][C@H:7]2[CH2:6][CH2:5][CH2:4][C@@H:3]([CH2:1][CH3:2])[N:13]2[C:12]1=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86706235tert-butyl (4S,7R,10aS)-7-ethyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Product 1

HCID 86706236(4S,7R,10aS)-4-amino-7-ethylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4S,7R,10aS)-7-ethyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (52 mg, 0.16 mmol) in DCM (1 mL) was added TFA (1.0 mL, 13 mmol). The reaction mixture was stirred at rt for 1 hr. The reaction mixture was concentrated and dried under high vacuum to afford (4S,7R,10aS)-4-amino-7-ethylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one trifluoroacetate (54 mg, 0.16 mmol, 100% yield) as an oil. Anal. Calcd. for C11H20N2OS m/z 228.3. found: 229.2 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-3b1c492c4e3348f6ba886c67b1ca8c3e
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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