Diisopropylethylamine → HCID 53630508, compound

HRID 1698443Notes

Reaction equation

HRID 1698443 reaction equation
ClCCl.CS(C)=O.C(N(C(C)C)CC)(C)C.[OH:17][C@@H:18]([C@@H:29]([NH:34][C:35]([C@@H:37]1[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])=[O:36])[CH2:30][CH2:31][CH2:32][CH3:33])[C:19]([NH:21][C@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[OH:28])=[O:20]>CS(C)=O>[O:20]=[C:19]([NH:21][C@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:28])[C:18](=[O:17])[C@@H:29]([NH:34][C:35]([C@@H:37]1[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])=[O:36])[CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21912085Dimethylsulfoxide-dichloromethaneHCID 53630499HCID 53630499, compound

Product 1

HCID 53630508HCID 53630508, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under argon gas stream, to 10 ml of an anhydrous dimethylsulfoxide-dichloromethane (1:1) solution containing 1.38 g (8.6 mmol) of sulfur trioxide pyridine complex salt were successively added dropwise at 0° C. 1.47 ml (8.6 mmol) of diisopropylethylamine, and then, 5 ml of an anhydrous dimethylsulfoxide solution containing 350 mg (0.7 mmol) of (2S)-N-[(2S,3S)-2-hydroxy-1-[N-[(1S,2S)-2-hydroxycyclohexane-1-yl]amino]-1-oxo-3-heptyl]-1-(phenylmethoxycarbonyl)pyrrolidine-2-carboxamide, and the resulting mixture was stirred at the same temperature for 5 hours. After completion of the reaction, to the reaction mixture was added 25 ml of ice-water, and the resulting mixture was extracted with 30 ml of ethylacetate three times. The organic layers were combined, washed with 100 ml of a 10%-aqueous citric acid solution, 100 ml of a saturated aqueous sodium hydrogen carbonate solution, and then, 100 ml of a saturated NaCl solution, dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The residue was purified by neutral silica gel column chromatography to obtain 300 mg (Yield: 86.1%) of the title compound.

Workup

  1. additionwere successively added dropwise at 0° C
  2. customAfter completion of the reaction
  3. extractionthe resulting mixture was extracted with 30 ml of ethylacetate three times
  4. washwashed with 100 ml of a 10%-aqueous citric acid solution, 100 ml of a saturated aqueous sodium hydrogen carbonate solution
  5. dry with material100 ml of a saturated NaCl solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by neutral silica gel column chromatography

Sources & evidence

ORD record
ord-13b517eb04e34fe59da5cf0a8f32217f
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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