Hydrochloric Acid → (4S,7S,10aS)-4-Amino-7-(methoxymethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one hydrochloride

HRID 529540Notes

Reaction equation

HRID 529540 reaction equation
[ClH:1].[CH3:2][O:3][CH2:4][C@H:5]1[N:15]2[C@@H:9]([S:10][CH2:11][CH2:12][C@H:13]([NH:17]C(=O)OC(C)(C)C)[C:14]2=[O:16])[CH2:8][CH2:7][CH2:6]1>>[ClH:1].[NH2:17][C@H:13]1[CH2:12][CH2:11][S:10][C@H:9]2[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:4][O:3][CH3:2])[N:15]2[C:14]1=[O:16]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86706224tert-butyl (4S,7S,10aS)-7-(methoxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Product 1

HCID 68292741(4S,7S,10aS)-4-Amino-7-(methoxymethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one hydrochlorideYield 93%

Procedure

A solution of HCl (4.0 N in dioxane, 1 mL) was added to a reaction flask containing tert-butyl (4S,7S,10aS)-7-(methoxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (83 mg, 0.24 mmol). The reaction mixture was then stirred at rt overnight. The reaction mixture was concentrated. Ether was added to the residue. A white solid formed. The mixture was stirred for 5 min and then filtered. The solid was dried under vacuum to give (4S,7S,10aS)-4-Amino-7-(methoxymethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one hydrochloride (63 mg, 0.22 mmol, 93% yield) as a white solid. Anal. Calcd. for C11H20N2O2S m/z 244.4. found: 245.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionEther was added to the residue
  3. customA white solid formed
  4. stirringThe mixture was stirred for 5 min
  5. filtrationfiltered
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-b56a3aa2acf74799ab0a3264d4856b2f
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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