Trityl chloride → HCID 10572222, compound

HRID 2218523Notes

Reaction equation

HRID 2218523 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)=[O:5])C.[C:12](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:12]([NH:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 10572222HCID 10572222, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the commercially available 2-amino-thiazole-4-carboxylic acid ethyl ester 2a (3.8 g, 22 mmol) and trityl chloride (6.8 g, 24.3 mmol) in 30 ml pyridine was stirred at room temperature for 16 hours. The precipitate was filtered off and the filtrate was concentrated to reduce the volume to 20 ml. To the crude 2-(trityl-amino)-thiazole-4-carboxylic acid ethyl ester in 20 ml pyridine was added a solution of sodium hydroxide (5.4 g) in 50 ml of 60% ethanol in water. The reaction mixture was stirred at room temperature over the weekend, and was then acidified with acetic acid to pH 5. The precipitate was collected and dried to give 2-(tritylamino)-thiazole-4-carboxylic acid as a white solid (6.1 g, 72% yield). LC/MS (m/z 385.08 (M−H)+); HPLC Rt: 3.732 min.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionTo the crude 2-(trityl-amino)-thiazole-4-carboxylic acid ethyl ester in 20 ml pyridine was added a solution of sodium hydroxide (5.4 g) in 50 ml of 60% ethanol in water
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-f1d5c2ad00e246058b5bde7a04d1e98f
Source dataset
uspto-grants-2008_08
Patent number
US07411071B2

Reaction notes

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