Hydrochloric Acid → HCID 178519962, compound

HRID 2169317Notes

Reaction equation

HRID 2169317 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:41]1[CH2:43][CH2:42]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+].O>O1CCCC1>[CH:41]1([N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:42][CH2:43]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 178455272HCID 178455272, compound

Product 1

HCID 178519962HCID 178519962, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amide (284) (430 mg, 0.69 mmol) in tetrahydrofuran (20 mL) was added 1N HCl (3.5 mL. 3.48 mmol) at room temperature and the reaction mixture was stirred for 30 min. After completion of the reaction, solid NaHCO3 was added, basified up to pH 8. Water (10 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The organic part was dried and concentrated to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid cyclopropyl-(2-hydroxyethyl)-amide (285) (300 mg, 88.4%) as a light yellow sticky mass.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  3. customThe organic part was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c27e38fb01e444bba04c23a8b8225800
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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