Hydrochloric Acid → (4S,7S,10aS)-4-amino-5-oxo-N-(thiazol-2-yl)octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxamide hydrochloride salt

HRID 529488Notes

Reaction equation

HRID 529488 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]([C:21](=[O:28])[NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)[N:3]12.[ClH:29]>O1CCOCC1>[ClH:29].[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]([C:21]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[O:28])[N:3]2[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86706202tert-butyl (4S,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Product 1

HCID 86706203(4S,7S,10aS)-4-amino-5-oxo-N-(thiazol-2-yl)octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxamide hydrochloride saltYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a round bottom flask was added tert-butyl (4S,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (35 mg, 0.082 mmol) and 4 M HCl in dioxane (1 mL). The mixture was stirred at rt for 1 h. The reaction mixture was concentrated to give (4S,7S,10aS)-4-amino-5-oxo-N-(thiazol-2-yl)octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxamide hydrochloride salt (30 mg, 0.082 mmol, 100% yield).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-99fb19d0ae254435b29126144d1c49a1
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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