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

HRID 376973Notes

Reaction equation

HRID 376973 reaction equation
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]

Participants

6

Reactant 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)

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7dc7550559884f719b667e77ef3e6b1a
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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