Ethyl Acetate → HCID 21891719, compound

HRID 720668Notes

Reaction equation

HRID 720668 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][C:7]=1[CH3:31])=[O:5])C.[OH-].[Na+].C(OCC)(=O)C>C(O)C.O>[CH3:31][C:7]1[N:8]=[C:9]([NH:11][C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:10][C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 58739232HCID 58739232, compound

Product 1

HCID 21891719HCID 21891719, compoundYield 11.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid ethyl ester (500 mg, 1.17 mmol) in ethanol (10 mL) at 25° C. was treated with a 1N aqueous sodium hydroxide solution (3.51 mL, 3.51 mmol). The resulting mixture was heated to 50° C. for 18 h. At this time, the reaction was treated with an additional amount of a 1N aqueous sodium hydroxide solution (3.6 mL, 3.6 mmol). This mixture was heated at 50° C. for an additional 8 days. At this time, the reaction was diluted with water (100 mL), acidified to pH=5, and treated with ethyl acetate. The resulting white solid was collected by filtration and dried in vacuo. The filtrate was extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 4-methyl-2-(trityl-amino)-thiazole-5-carboxylic acid (55.7 mg, 11.9%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ9.09 (broad s, 1H), 7.22 (m, 15 H), 2.22 (s, 3H).

Workup

  1. temperatureThis mixture was heated at 50° C. for an additional 8 days
  2. filtrationThe resulting white solid was collected by filtration
  3. customdried in vacuo
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02a5209054e24bbf8939a90205d1be0d
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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