Benzoyl chloride → HCID 14696315, compound

HRID 1200153Notes

Reaction equation

HRID 1200153 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:32])[C@@H:12]([NH:24][C:25]([O:27]C(C)(C)C)=O)[CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.C(Cl)(=O)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[CH3:9][C:2]([NH:10][C:11](=[O:32])[C@@H:12]([NH:24][C:25](=[O:27])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 53917307HCID 53917307, compound

Product 1

HCID 14696315HCID 14696315, compoundYield 49.2%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

13.3 g of (2R)-N-(α,α-dimethylbenzyl)-2-(t-butoxycarbonylamino)-3-(p-methoxybenzylthio)propionamide (prepared as described in Preparation 6) were dissolved in 50 ml of toluene. To this solution were added 4.70 ml of triethylamine, and then 2.23 g of benzoyl chloride was added slowly to the mixture, whilst ice-cooling. The reaction solution was stirred for 70 minutes, and then ethyl acetate was added to it, after which it was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was purified by column chromatography through 210 g of silica gel. From the fraction eluted with hexane containing 30-40% v/v ethyl acetate, were obtained 4.31 g of an oily substance. This substance was dissolved in a mixture of ethyl acetate and hexane, and, after removal of crystals which had separated out (about 250 mg, melting at 189° C.), concentration of the mother liquor gave 3.61 g of the title compound as a glassy substance, [α]25 =-25.3° (C=1, CHCl3).

Workup

  1. temperaturecooling
  2. washafter which it was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe resulting residue was purified by column chromatography through 210 g of silica gel
  6. washFrom the fraction eluted with hexane containing 30-40% v/v ethyl acetate
  7. customwere obtained 4.31 g of an oily substance
  8. customafter removal of crystals which
  9. customhad separated out (about 250 mg, melting at 189° C.), concentration of the mother liquor

Sources & evidence

ORD record
ord-7bac3c5d51e84a9a837731f77c6a7202
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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