Trityl chloride → Ethyl 2-oxo-2-(2-(tritylamino)thiazol-4-yl)acetate

HRID 1534456Notes

Reaction equation

HRID 1534456 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1.[C:21]1([C:27]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)Cl)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O.C(Cl)Cl>[C:21]1([C:27]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

Product 1

HCID 13151727Ethyl 2-oxo-2-(2-(tritylamino)thiazol-4-yl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

27 g of triethylamine are added to a solution of 90 g of ethyl 2-aminothiazol-4-ylglyoxylate in 225 ml of dimethylformamide and 375 ml of CH2Cl2 at -15° and 75 g of triphenylchloromethane are then added at -30°. After 15 minutes at -30°, the mixture is stirred for 3 hours without a cooling bath and 500 ml of CH2Cl2 are added to the resulting reaction mixture, the mixture is washed with 300 ml of 1N HCl and then twice with 200 ml of water, the organic phase is dried over Na2SO4 and the solvent is evaporated off.

Workup

  1. washthe mixture is washed with 300 ml of 1N HCl
  2. dry with materialtwice with 200 ml of water, the organic phase is dried over Na2SO4
  3. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-9b992c67c5074206b6063bdb54d48033
Source dataset
uspto-grants-1992_02
Patent number
US05089490

Reaction notes

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