Hydrochloric Acid → HCID 178457435, compound

HRID 2169275Notes

Reaction equation

HRID 2169275 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[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]([Br: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>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[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]([Br:41])=[CH:37][CH:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178457471HCID 178457471, compound

Product 1

HCID 178457435HCID 178457435, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-[1-(4-bromophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]isopropylamide (232) (1.0 g, 1.46 mmol) in tetrahydrofuran (10 mL) was added HCl (37% aqueous, 1.70 mmol) and the reaction mixture was stirred at room temperature for 1.5 h. After completion of the reaction, the mixture was diluted with ethyl acetate (30 mL), washed with water, separated and the organic phase dried over Na2SO4. After evaporation of the solvent, the crude product was purified by 100-200 silica gel column chromatography using 60% ethyl acetate in hexane followed by 5% methanol in dichloromethane as the eluent to obtain 5-benzyloxy-2-[1-(4-bromophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (233) (0.7 g, 84%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water
  3. customseparated
  4. dry with materialthe organic phase dried over Na2SO4
  5. customAfter evaporation of the solvent
  6. customthe crude product was purified by 100-200 silica gel column chromatography

Sources & evidence

ORD record
ord-d57f3edbc4fc416da1978f4c625c5a66
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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