Ethyl Acetate → HCID 178524881, compound

HRID 2169435Notes

Reaction equation

HRID 2169435 reaction equation
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2([N:29]3[C:33]4=[N:34][CH:35]=[CH:36][CH:37]=[C:32]4[CH:31]=[CH:30]3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O.[OH-].[Li+].C(OCC)(=O)C>O1CCCC1.O>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2([N:29]3[C:33]4=[N:34][CH:35]=[CH:36][CH:37]=[C:32]4[CH:31]=[CH:30]3)[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178450821HCID 178450821, compound

Product 1

HCID 178524881HCID 178524881, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (403) (900 mg. 1.8 mmol) in a mixture of tetrahydrofuran:water (2:1) (30 mL) was added lithium hydroxide monohydrate (756 g, 18.0 mmol) and the mixture was refluxed for 24 h (TLC, ethyl acetate, Rf=0.1). After completion of reaction, volatiles were evaporated and the aqueous part was washed with ethyl acetate (3×30 mL). The aqueous layer was acidified with HCl (6N) to pH 3 and extracted with ethyl acetate (3×50 mL). The organic phase was thereafter dried and concentrated to get 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl methyl)-pyrimidine-4-carboxylic acid (404) (500 mg, 62%) as an off-white sticky solid.

Workup

  1. customAfter completion of reaction, volatiles
  2. customwere evaporated
  3. washthe aqueous part was washed with ethyl acetate (3×30 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. customThe organic phase was thereafter dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ab30852c0fea4b81bc94022abbad6e89
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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