Sodium hydride → HCID 54199144, compound

HRID 1901346Notes

Reaction equation

HRID 1901346 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:35][C:36]1[S:40][C:39]2[CH:41]=[CH:42][C:43]([C:45]#[N:46])=[CH:44][C:38]=2[CH:37]=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH2:35][C:36]2[S:40][C:39]3[CH:41]=[CH:42][C:43]([C:45]#[N:46])=[CH:44][C:38]=3[CH:37]=2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 135679672-(Bromomethyl)-1-benzothiophene-5-carbonitrileHCID 54022452ethyl 2-[4-[((2R)-1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxy]phenyl]-2-ethoxycarbonylacetate

Product 1

HCID 54199144HCID 54199144, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.1 g of ethyl 2-[4-[((2R)-1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxy]phenyl]-2-ethoxycarbonylacetate was dissolved in 100 ml of tetrahydrofuran. At room temperature, the thus prepared solution was mixed with 0.38 g of 60% sodium hydride and stirred for 30 minutes. With stirring at room temperature, to the resulting reaction solution was added dropwise 10 ml of a tetrahydrofuran solution containing 2.1 g of 2-bromomethylbenzo[b]thiophene-5-carbonitrile. After concentrating the reaction solution to dryness, the resulting residue was purified by subjecting it to silica gel column chromatography using a toluene/chloroform mixture as an elution solvent, thereby obtaining 4.34 g of the title compound in an oily form.

Workup

  1. stirringWith stirring at room temperature, to the resulting reaction solution
  2. concentrationAfter concentrating the reaction solution to dryness
  3. customthe resulting residue was purified

Sources & evidence

ORD record
ord-5ac30cce8f0e429ba43f9d4a6142ffbe
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Reaction notes

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