Sodium hydride → HCID 54199144, compound

HRID 53981Notes

Reaction equation

HRID 53981 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-e15e291ca19f416f898005dd475e3ff8
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Reaction notes

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