Hydrochloric Acid → HCID 178519971, compound

HRID 2169370Notes

Reaction equation

HRID 2169370 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:42]1[CH2:47][CH2:46][O:45][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>[OH:8][CH2:9][CH2:10][N:11]([CH:42]1[CH2:43][CH2:44][O:45][CH2:46][CH2:47]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=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)[CH2:31][CH2:32][CH2:33][CH2:34]2)[N:15]=1)=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178455280HCID 178455280, compound

Product 1

HCID 178519971HCID 178519971, 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]-(tetrahydro-pyran-4-yl)-amide (333) in tetrahydrofuran (3 ml) was added 1N HCl (1 ml) at room temperature and the reaction mixture was stirred for 30 min at room temperature while silica thin layer chromatography was performed (ethyl acetate:hexane=3:2, Rf=0.4). After completion of the reaction, solid NaHCO3 was added and the mixture basified up to about pH 8. After extraction 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 (2-hydroxyethyl)-(tetrahydro-pyran-4-yl)-amide (334) which was used in the next step without purification.

Workup

  1. additionwas added
  2. extractionAfter extraction with ethyl acetate (3×30 mL)
  3. customthe combined extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb05933f1be34084bd42019dc9e1ffa7
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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