Hydrochloric Acid → HCID 178457446, compound

HRID 2169252Notes

Reaction equation

HRID 2169252 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:43]([CH3:45])[CH3:44])[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]=[C:39]([Cl:41])[CH:38]=[CH:37][C:36]=3[Cl:42])[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:43]([CH3:45])[CH3:44])[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]=[C:39]([Cl:41])[CH:38]=[CH:37][C:36]=3[Cl:42])[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 178457482HCID 178457482, compound

Product 1

HCID 178457446HCID 178457446, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (206) (250 mg, 0.37 mmol) in tetrahydrofuran (3.3 mL) was added 1N HCl (1.9 mL, 1.86 mmol) at room temperature and the mixture was stirred for 2 h at room temperature. Silica thin layer chromatography was performed (50% ethyl acetate in hexane, Rf=0.2). After completion of the reaction, the mixture was basified (pH ˜8) with a saturated solution of NaHCO3, extracted with ethyl acetate, dried over sodium sulfate and concentrated to get a crude product which was purified by a CombiFlash column (eluted at 30% ethyl acetate in hexane) to get 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (207) (200 mg, 96.26%) as a white foam-like solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto get a crude product which
  6. customwas purified by a CombiFlash column (eluted at 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e85f78f17f5e4e06ae1039d58d471864
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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