Trityl chloride → HCID 86592480, compound

HRID 496246Notes

Reaction equation

HRID 496246 reaction equation
Cl.[NH2:2][CH:3]([CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([O:11][CH3:12])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[C:19](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[C:19]([NH:2][CH:3]([CH:8]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:9]([O:11][CH3:12])=[O:10])[C:4]([O:6][CH3:7])=[O:5])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 86592481HCID 86592481, compound

Product 1

HCID 86592480HCID 86592480, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5 g (18.5 mmol) of 2-amino-3-phenyl-succinic acid, dimethyl ester hydrochloride in CH2Cl2 (100 mL) was added 7.7 mL (56 mmol) of TEA followed by 6.2 g (22.1 mmol) of trityl chloride. The reaction was stirred at rt for 2 days and then concentrated in vacuo. Et2O was added to the crude residue and the mixture was filtered through a pad of silica gel and concentrated in vacuo to give a colorless oil. The residue was purified by flash column chromatography on silica gel eluted with 3:1 hexanes:Et2O to yield 6 g of 2-(N-tritylamino)-3-phenyl-succinic acid, dimethyl ester as a white solid. The product was a 1.3:1 mixture of diastereomers as judged by 1H-NMR analysis.

Workup

  1. concentrationconcentrated in vacuo
  2. additionEt2O was added to the crude residue
  3. filtrationthe mixture was filtered through a pad of silica gel
  4. concentrationconcentrated in vacuo
  5. customto give a colorless oil
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluted with 3:1 hexanes

Sources & evidence

ORD record
ord-ed3cb803b3564b36a9d25387820965bd
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

Loading…