Lithium Hydroxide → 4-Tert-Butyl-2-(4-methyl-benzoylamino)-4H-pyrrolo[2,3-d]thiazole-6-carboxylic acid

HRID 1594225Notes

Reaction equation

HRID 1594225 reaction equation
C([O:3][C:4]([C:6]1[C:13]2[S:12][C:11]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[N:10][C:9]=2[N:8]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:7]=1)=[O:5])C.[OH-].[Li+]>C1COCC1.O>[C:24]([N:8]1[C:9]2[N:10]=[C:11]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[S:12][C:13]=2[C:6]([C:4]([OH:5])=[O:3])=[CH:7]1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 590013684-Tert-Butyl-2-(4-methyl-benzoylamino)-4H-pyrrolo[2,3-d]thiazole-6-carboxylic acid ethyl ester

Product 1

HCID 590012694-Tert-Butyl-2-(4-methyl-benzoylamino)-4H-pyrrolo[2,3-d]thiazole-6-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Water (50 ml) was added to a stirred suspension of 4-tert-butyl-2-(4-methyl-benzoylamino)-4H-pyrrolo[2,3-d]thiazole-6-carboxylic acid ethyl ester (4.0 g, 10.5 mmol) and lithium hydroxide (1.0 g, 42.6 mmol) in THF (105 ml). The mixture was held at reflux for 18 hours, cooled, diluted with water (200 ml), and washed with ethyl acetate. The aqueous phase was chilled, then acidified (6M HCl), with stirring, to precipitate product. The solid was filtered and dried to yield 3.14 g (84%) of the product. MS: M+H=358.

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. washwashed with ethyl acetate
  4. temperatureThe aqueous phase was chilled
  5. customto precipitate product
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-542ea5e57d314512abc5416692415a32
Source dataset
uspto-grants-2007_11
Patent number
US07300949B2

Reaction notes

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