Hydrochloric Acid → HCID 178519969, compound

HRID 2169362Notes

Reaction equation

HRID 2169362 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:42]1[CH2:44][CH2:43]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][C:38]([Cl:41])=[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(OCC)(=O)C.C([O-])(O)=O.[Na+]>O1CCCC1.CCCCCC>[CH:42]1([N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=4)[CH2:31][CH2:32][CH2:33][CH2:34]3)[N:15]=2)=[O:13])[CH2:44][CH2:43]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178455278HCID 178455278, compound

Product 1

HCID 178519969HCID 178519969, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amide (325) (100 mg, 0.16 mmol) in tetrahydrofuran was added 1N HCl (5 ml) at room temperature and stirring was continued for 30 min wile silica thin layer chromatography was performed (60% ethyl acetate in hexane; Rf=0.4). After completion of the reaction, solid NaHCO3 was added to the reaction mixture which was basified up to about pH 8 and extracted with ethyl acetate (3×30 mL). The combined extracts were dried and concentrated to get 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid cyclopropyl-(2-hydroxyethyl)-amide (326) as a brown sticky mass. This was used in the next step without purification.

Workup

  1. additionwas added to the reaction mixture which
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. customThe combined extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d039006f7894cc4816624d8fb9db677
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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