Sodium hydride → 2-Benzoyloxymethyl-5-{[tert-butoxycarbonyl(6,2'-dimethyl-4'-propionyl-biphenyl-3-yl)amino]methyl}benzyl benzoate

HRID 584324Notes

Reaction equation

HRID 584324 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22][CH3:23])=[CH:17][C:16]=2[CH3:25])[C:11]([CH3:14])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:29]([O:37][CH2:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[CH2:47][O:48][C:49](=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:42]Br)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[C:29]([O:37][CH2:38][C:39]1[CH:40]=[C:41]([CH2:42][N:7]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:26])[C:8]2[CH:9]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22][CH3:23])=[CH:17][C:16]=3[CH3:25])[C:11]([CH3:14])=[CH:12][CH:13]=2)[CH:44]=[CH:45][C:46]=1[CH2:47][O:48][C:49](=[O:56])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 223456183,4-Bis(benzoyloxymethyl)benzyl bromideHCID 22345642Tert-butyl(6,2'-dimethyl-4'-propionylbiphenyl-3-yl)carbamate

Product 1

HCID 697928892-Benzoyloxymethyl-5-{[tert-butoxycarbonyl(6,2'-dimethyl-4'-propionyl-biphenyl-3-yl)amino]methyl}benzyl benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

900 mg (2.5 mmol) of tert-butyl(6,2′-dimethyl-4′-propionylbiphenyl-3-yl)carbamate are dissolved in 30 ml of dimethylformamide. 110 mg (2.8 mmol) of 60% sodium hydride are added and the medium is stirred for 15 minutes. 1.23 g (2.8 mmol) of 3,4-bis(benzoyloxymethyl)benzyl bromide are then added and the medium is stirred for 12 hours at room temperature. After the usual work-up, the residue obtained is purified by chromatography on a column of silica (eluent: 8 heptane/2 ethyl acetate). A colorless oil is obtained (m=1 g, Y=55%).

Workup

  1. stirringthe medium is stirred for 12 hours at room temperature
  2. customAfter the usual work-up, the residue obtained
  3. customis purified by chromatography on a column of silica (eluent: 8 heptane/2 ethyl acetate)
  4. customA colorless oil is obtained (m=1 g, Y=55%)

Sources & evidence

ORD record
ord-ca14fcc31f5f4c098bd1bace29433037
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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