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 2417770ノート

反応式

HRID 2417770 の反応式
Br.[CH3:2][O:3][C:4]([C@@H:6]1[CH2:14][C:9]2([S:13][CH2:12][CH2:11][S:10]2)[CH2:8][NH:7]1)=[O:5]>[OH-].[Na+]>[CH3:2][O:3][C:4]([C@@H:6]1[CH2:14][C:9]2([S:10][CH2:11][CH2:12][S:13]2)[CH2:8][NH:7]1)=[O:5]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

Dissolve the 1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid methyl ester hydrobromide from paragraph B in 0.1 N 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-benzyloxycarbonyl-(S)-alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid, methyl ester, a yellow oil [α]D26 =-14.8° (ethanol).

後処理

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

出典と根拠

ORDレコード
ord-5a6c40e53d50424aaccf3fcf8c67aea1
出典データセット
uspto-grants-1984_09
特許番号
US04470972

反応ノート

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