Hydrogen Bromide → 3(S)-amino-3,4-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 53123Notes

Reaction equation

HRID 53123 reaction equation
C([NH:11][C@H:12]1[C:18](=[O:19])[NH:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[S:14][CH2:13]1)(OCC1C=CC=CC=1)=O.Br.C(=O)=O>C(O)(=O)C>[NH2:11][C@H:12]1[C:18](=[O:19])[NH:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[S:14][CH2:13]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 280Carbon DioxideHCID 207031603(S)-[(Carbobenzyloxy)amino]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 109104143(S)-amino-3,4-dihydro-1,5-benzothiazepin-4(5H)-oneYield 46.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6.2 g (18.9 mmol) of 3(S)-[(carbobenzyloxy)amino]-2,3 dihydro-1,5-benzothiazepin-4(5H)-one and 25 mL of a 30% HBr solution in acetic acid was stirred at room temperature for 1 hour. There was noticeable evolution of carbon dioxide gas (CO2) and the initial suspension gradually went into solution. After solution was obtained, a heavy precipitate was formed. The precipitate was filtered, and the solid triturated with 75 mL of NaHCO3 and 75 mL of ethyl acetate. The ethyl acetate layer was dried and evaporated. The residue was triturated to yield 1.7 g of product as a white solid. Neutralization of the filtrate and extraction yielded an additional 1.15 g of product. The two solids were combined to yield 2.85 g (78%) of 3-(S)-amino-2,3-dihydro-1,5-benthiazepin-4(5H)-one.

Workup

  1. customAfter solution was obtained
  2. customa heavy precipitate was formed
  3. filtrationThe precipitate was filtered
  4. customthe solid triturated with 75 mL of NaHCO3 and 75 mL of ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. customevaporated
  7. customThe residue was triturated

Sources & evidence

ORD record
ord-3aea94c452374cf784a9d73c810d5085
Source dataset
uspto-grants-1997_04
Patent number
US05618808

Reaction notes

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