Water → HCID 18948470, compound

HRID 1768591Notes

Reaction equation

HRID 1768591 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]([CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[CH2:10][CH:11]([CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].O>CS(C)=O>[O:34]1[CH2:33][CH2:32][N:31]([CH2:30][C:9](=[O:8])[CH2:10][CH:11]([CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 18948430HCID 18948430, compound

Product 1

HCID 18948470HCID 18948470, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.3 g (14.7 mmole) of a sulfur trioxide/pyridine complex and 2.1 ml of triethylamine were added at room temperature to a solution of 1.96 g (4.91 mmole) of t-butyl 4-hydroxy-5-morpholino-2-(1-naphthylmethyl)pentanoate (prepared as described in Preparation 12) dissolved in 20 ml of anhydrous dimethyl sulfoxide. The mixture was stirred for 6 hours, allowed to stand overnight and then mixed with water, after which it was extracted with ethyl acetate. The organic layer was washed with water and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous magnesium sulfate. It was then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: a 10: 90 by volume mixture of methanol and methylene chloride), to afford 1.30 g (66.7%) of the title compound as a pale brown oil.

Workup

  1. waitto stand overnight
  2. extractionafter which it was extracted with ethyl acetate
  3. washThe organic layer was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationIt was then concentrated by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel (eluent
  7. additiona 10: 90 by volume mixture of methanol and methylene chloride),

Sources & evidence

ORD record
ord-940bdc4fe7814fa18b9728e40d4a4209
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

Loading…