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

HRID 529483Notes

Reaction equation

HRID 529483 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C@H:6]1[N:16]2[C@@H:10]([S:11][CH2:12][CH2:13][C@H:14]([NH:18]C(=O)OC(C)(C)C)[C:15]2=[O:17])[CH2:9][CH2:8][CH2:7]1.[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>C(Cl)Cl>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[NH2:18][C@H:14]1[CH2:13][CH2:12][S:11][C@H:10]2[CH2:9][CH2:8][CH2:7][C@@H:6]([C:2]3[O:1][CH:5]=[N:4][N:3]=3)[N:16]2[C:15]1=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68311017tert-butyl (4S,7S,10aS)-7-(1,3,4-oxadiazol-2-yl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Product 1

HCID 68292026(4S,7S,10aS)-4-Amino-7-(1,3,4-oxadiazol-2-yl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one 2,2,2-trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4S,7S,10aS)-7-(1,3,4-oxadiazol-2-yl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (22 mg, 0.060 mmol) in DCM (0.6 mL) at 0° C., was added TFA (0.323 mL, 4.20 mmol). The mixture was stirred at rt for 1.5 hr. The reaction was concentrated to give (4S,7S,10aS)-4-amino-7-(1,3,4-oxadiazol-2-yl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5 (7H)-one 2,2,2-trifluoroacetate (23 mg, 0.060 mmol, 100% yield). Anal. Calcd. for C11H16N4O2S m/z 268.4. found: 269.2 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-068550a77097486aba9a85f67b005795
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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