2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid → N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

HRID 1796159ノート

反応式

HRID 1796159 の反応式
C1(N=C=N)CCCCC1.[CH3:10][CH:11]([CH3:30])[CH2:12][S:13]([CH2:16][CH:17]([CH2:21][C:22]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[C:18]([OH:20])=O)(=[O:15])=[O:14].[NH2:31][CH:32]([CH2:46][CH3:47])[C@@H:33]([C:35]1[N:39]=[C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:37][N:36]=1)[OH:34]>C(Cl)Cl>[OH:34][CH:33]([C:35]1[N:39]=[C:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:37][N:36]=1)[C@@H:32]([NH:31][C:18](=[O:20])[CH:17]([CH2:16][S:13]([CH2:12][CH:11]([CH3:10])[CH3:30])(=[O:14])=[O:15])[CH2:21][C:22]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[CH2:46][CH3:47]

参加物

5

反応物 3

HCID 115659842-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acidHCID 12048208N-CyclohexylcarbodiimideHCID 67301524(S)-2-Amino-1-(5-phenyl-1,2,4-oxadiazol-3-yl)-butan-1-ol

生成物 1

HCID 11635192N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A suspension of PS-bound N-cyclohexylcarbodiimide (HL 200–400 mesh cross linked with 2% DVB) from Novabiochem (436 mg, 0.841 mmol, 1.93 mmol/g loading) in methylene chloride (6 mL) was treated with 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid (154 mg, 0.480 mmol) in methylene chloride (3 mL) and stirred at room temperature for 10 minutes. A solution of (S)-2-Amino-1-(5-phenyl-1,2,4-oxadiazol-3-yl)-butan-1-ol (96 mg, 0.412 mmol) in methylene chloride (3 mL) was added and the reaction mixture was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was evaporated under reduced pressure. Crude purified by flash chromatography eluting with a mixture of ethyl acetate and heptane to give N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide as an off white solid (41 mg) (mixture of diastereoisomers).

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 3 h
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customCrude purified by flash chromatography
  5. washeluting with a mixture of ethyl acetate and heptane

出典と根拠

ORDレコード
ord-7b24e8a1287d4d0ea447c337135f8c1a
出典データセット
uspto-grants-2006_04
特許番号
US07030116B2

反応ノート

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