Dichloromethane → HCID 67745419, compound

HRID 1735417Notes

Reaction equation

HRID 1735417 reaction equation
C(N(CC)CC)C.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].C(Cl)Cl.[OH:19][CH:20]([C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:36]([NH:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])=[O:30])[CH2:21][CH2:22][OH:23]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Si:8]([O:23][CH2:22][CH2:21][CH:20]([C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:36]([NH:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])=[O:30])[OH:19])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 67745431HCID 67745431, compound

Product 1

HCID 67745419HCID 67745419, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Triethylamine (0.5 ml), 4-dimethylaminopyridine (20 mg) and tert-butyldimethylsilyl chloride (497 mg) were added to a methylene chloride solution (6 ml) of (S)-2-[[(S)-2-(1,3-dihydroxypropyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (1.13 g), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate and saturated brine in order, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (eluent: chloroform-methanol) to give the title compound (1.02 g).

Workup

  1. washwashed with saturated sodium hydrogencarbonate and saturated brine in order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2dc6873734754a49b780e8037cca8f11
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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