1,4-dithia-7-azaspiro [4.4]nonane-8(S)-carboxylic acid, methyl ester hydrobromide → Methyl (8S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylate

HRID 2226402노트

반응식

HRID 2226402 반응식
Br.[S:2]1[C:6]2([CH2:10][C@@H:9]([C:11]([O:13][CH3:14])=[O:12])[NH:8][CH2:7]2)[S:5][CH2:4][CH2:3]1>[OH-].[Na+]>[S:2]1[C:6]2([CH2:10][C@@H:9]([C:11]([O:13][CH3:14])=[O:12])[NH:8][CH2:7]2)[S:5][CH2:4][CH2:3]1

참가 물질

3

반응물 1

HCID 132746721,4-dithia-7-azaspiro [4.4]nonane-8(S)-carboxylic acid, methyl ester hydrobromide

생성물 1

HCID 13274671Methyl (8S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylate

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

Dissolve the 1,4-dithia-7-azaspiro[4.4]nonane-8-(S)-carboxylic acid, methyl ester, hydrobromide from paragraph B in 0.1N NaOH and extract with ethyl acetate. Dry the organic layer over magnesium sulfate and concentrate in vacuo to give 1,4-dithia-7-azaspiro [4.4]nonane-8(S)-carboxylic acid, methyl ester (1.35 g). Dissolve the latter in 100 ml of ethyl acetate and treat with 2.07 g of N-benzyloxycarbonyl-(S)-alanine, N-hydroxysuccinimide ester. Stir the reaction mixture at room temperature for eighteen hours and concentrate in vacuo. Place the residue on a column of silica gel (300 g, 60-200 mesh) and elute with hexane:ethyl acetate 4:1 to obtain 7-[N-benzyloxy-carbonyl-(S)-alanyl]-1,4-dithia-7-azaspiro[4.4 ]nonane-8(S)-carboxylic acid, methyl ester, a yellow oil [α]D26 -14.8° (ethanol).

후처리

  1. extractionextract with ethyl acetate
  2. dry with materialDry the organic layer over magnesium sulfate
  3. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-3199e928d7c548c591f318bec0626d04
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05348944

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