Water → [4-(2-Methyl-2-morpholin-4-yl-propionyl)-phenylthio]-acetic acid 2,2-bis-mercaptoacetoxymethyl-butyl ester

HRID 376973노트

반응식

HRID 376973 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([CH3:17])([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.[SH:19][CH2:20][C:21]([OH:23])=[O:22].[SH:24][CH2:25][C:26](O)=O.[SH:29]CC(O)=O.[CH2:34]([C:36](CO)(CO)[CH2:37][CH3:38])O.[H-].[Na+].[OH2:45].CN(C)[CH:48]=[O:49]>>[SH:24][CH:25]([SH:29])[C:26]([O:49][CH2:48][CH:34]([O:22][C:21](=[O:23])[CH2:20][S:19][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([CH3:17])([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1)[CH2:36][CH2:37][CH3:38])=[O:45]

참가 물질

6

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 154053051-(4-Fluorphenyl)-2-methyl-2-morpholino-1-propanoneHCID 200270032-Ethyl-2-(hydroxymethyl)propane-1,3-diol;tris(2-sulfanylacetic acid)

생성물 1

HCID 54326548[4-(2-Methyl-2-morpholin-4-yl-propionyl)-phenylthio]-acetic acid 2,2-bis-mercaptoacetoxymethyl-butyl ester

실험 절차

1.26 g (5.0 mmol) of 1-(4-fluorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one and 7.0 ml (25.0 mmol) of trimethylolpropane tris(2-mercaptoacetate) are dissolved in 25 ml of dry dimethylformamide, and 10.0 mmol of sodium hydride are added. The solution is stirred at room temperature for 2 h. Then the solution is poured into water. The crude product is extracted with methylene chloride, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with methylene chloride-methanol (100:1) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 0.93 (t, 3H), 1.31 (s, 6H), 1.44 (q, 2H), 1.95-2.13 (m, 2H), 2.57 (t, 4H), 3.25-3.32 (m, 6H), 3.70 (t, 4H), 4.10-4.15 (m, 6H), 7.33 (d, 2H), 8.51 (d, 2H).

후처리

  1. extractionThe crude product is extracted with methylene chloride
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel with methylene chloride-methanol (100:1) as an eluent

출처 및 근거

ORD 기록
ord-7dc7550559884f719b667e77ef3e6b1a
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022906

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