Water → 1-(Tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-(phthalimidoacetylamino)benzene

HRID 636492Notes

Reaction equation

HRID 636492 reaction equation
[NH2:1][C:2]1[C:3]([CH3:28])=[C:4]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([CH3:8])=[CH:6][CH:7]=1.[C:29]1(=[O:43])[N:33]([CH2:34][C:35](Cl)=[O:36])[C:32](=[O:38])[C:31]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:30]12.O>N1C=CC=CC=1.CN(C)C=O>[Si:11]([O:10][CH2:9][C:4]1[C:5]([CH3:8])=[CH:6][CH:7]=[C:2]([NH:1][C:35](=[O:36])[CH2:34][N:33]2[C:32](=[O:38])[C:31]3=[CH:39][CH:40]=[CH:41][CH:42]=[C:30]3[C:29]2=[O:43])[C:3]=1[CH3:28])([C:24]([CH3:25])([CH3:27])[CH3:26])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 962WaterHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 107391063-Amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene

Product 1

HCID 105074021-(Tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-(phthalimidoacetylamino)benzeneYield 94.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene (42.4 g) in pyridine (17.2 g) and dimethylformamide (212 ml) was dropwise added phthalimidoacetyl chloride (25.6 g) over the period of 15 minutes under ice-cooling, and the mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added water, and the resulting precipitates were collected by filtration and washed with acetonitrile to give 1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-(phthalimidoacetylamino)benzene (59.1 g) as colorless crystals.

Workup

  1. customover the period of 15 minutes
  2. temperaturecooling
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with acetonitrile

Sources & evidence

ORD record
ord-75f73dd2c7e74aa9bea5384e06a66f71
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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