Water → HCID 86606418, compound

HRID 2218524Notes

Reaction equation

HRID 2218524 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26]([OH:28])=[O:27])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].I[CH2:32][CH2:33][CH3:34].O>CS(C)=O.C(OCC)(=O)C>[CH2:32]([O:27][C:26]([C:24]1[N:25]=[C:21]([NH:20][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:22][CH:23]=1)=[O:28])[CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 10572222HCID 10572222, compound

Product 1

HCID 86606418HCID 86606418, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(trityl-amino)-thiazole-4-carboxylic acid (400 mg, 1.03 mmol) in DMSO (1 ml) was added KOH (215 mg, 1.55 mmol) followed by addition of 1-iodo-propane (263 mg, 1.55 mmol). The reaction was heated at 60° C. for 1 hour. It was taken into water and ethyl acetate. After separation, the organic layer was washed, dried and evaporated. The obtained crude product was purified via flash column (silica gel, 10% ethyl acetate in hexane) to yield 2-(trityl-amino)-thiazole-4-carboxylic acid propyl ester as a white solid (325 mg, 76%). LC/MS (m/z 429.14 (M+H)+); HPLC Rt: 4.182 min.

Workup

  1. customAfter separation
  2. washthe organic layer was washed
  3. customdried
  4. customevaporated
  5. customThe obtained crude product
  6. customwas purified via flash column (silica gel, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-97cf2a5b262447cfb1b4bb75ce532320
Source dataset
uspto-grants-2008_08
Patent number
US07411071B2

Reaction notes

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