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

HRID 53123ノート

反応式

HRID 53123 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3aea94c452374cf784a9d73c810d5085
出典データセット
uspto-grants-1997_04
特許番号
US05618808

反応ノート

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