Lithium hydroxide, monohydrate → N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine

HRID 275626ノート

反応式

HRID 275626 の反応式
C[O:2][C:3](=[O:41])[CH:4]([CH2:35][C:36]1[N:37]=[CH:38][S:39][CH:40]=1)[NH:5][C:6](=[O:34])[C@@H:7]([CH2:15][S:16]([C:19]([CH3:33])([C:21](=[O:32])[N:22]([CH3:31])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH3:20])(=[O:18])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:33][C:19]([S:16]([CH2:15][C@@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:6]([NH:5][CH:4]([C:3]([OH:41])=[O:2])[CH2:35][C:36]1[N:37]=[CH:38][S:39][CH:40]=1)=[O:34])(=[O:18])=[O:17])([C:21](=[O:32])[N:22]([CH3:31])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH3:20]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 54195495N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine methyl ester

生成物 1

HCID 18659451N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine収率 124.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 300 mg of N-[(S)-α-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine methyl ester in 2.5 ml of dioxan was treated with a solution of 24.3 mg of lithium hydroxide hydrate in 1 ml of water and stirred at 50 for 3 hours. Subsequently, the solution was partitioned between ethyl acetate and water and the organic phase was extracted three times with water. The aqueous extracts were adjusted to pH 2 with ethyl acetate and with 2N hydrochloric acid and evaporated under reduced pressure. There were obtained 365 mg of N-[(S)-α-[[[1 -methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D ,L-alanine as a colourless foam which was used directly in the next step.

後処理

  1. customSubsequently, the solution was partitioned between ethyl acetate and water
  2. extractionthe organic phase was extracted three times with water
  3. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-e57d4348d3e94caba79d3cc533542fc7
出典データセット
uspto-grants-1995_02
特許番号
US05393875

反応ノート

読み込み中…