Benzoyl chloride → HCID 89962592, compound

HRID 337987Notes

Reaction equation

HRID 337987 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:14][C@H:13]([OH:15])[C@@H:12]([C:16]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[N:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([O:34][C@H]1CC[C@H](O)[C@@H](C2N(COCCOC)N=CC=2)C1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.C(Cl)(=O)C1C=CC=CC=1>CN(C1C=CN=CC=1)C.ClC(Cl)C.O>[C:27]([O:15][C@H:13]1[CH2:14][C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:11][C@@H:12]1[C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[N:19]=[CH:18][CH:17]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 89962161HCID 89962161, compoundHCID 89963684HCID 89963684, compound

Product 1

HCID 89962592HCID 89962592, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of the mixture (2.99 g, 8.30 mmol) of (1S*,2R*,5R*)-5-(benzyloxy)-2-{1-[(2-methoxyethoxy)methyl]-1H-pyrazol-5-yl}cyclohexanol and (1S*,2R*,4S*)-4-(benzyloxy)-2-{1-[(2-methoxyethoxy)methyl]-1H-pyrazol-5-yl}cyclohexanol prepared in Example 155b, triethylamine (4.62 mL, 33.2 mmol), 4-(N,N-dimethylamino)pyridine (203 mg, 1.66 mmol) in dichloroethane (30 mL), and benzoyl chloride (1.93 mL, 16.6 mmol) was added, and the reaction solution was stirred for 5 hours under heated reflux. To the reaction solution, water (100 mL) was added, and an organic layer was extracted and then dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with column chromatography (hexane/ethyl acetate=1:9) to yield the title compound (2.72 g, 71%) as a mixture (2.72 g, 71%) with (1R*,2R*,4S*)-4-(benzyloxy)-2-[(1-[(2-methoxyethoxy)methyl]-1H-pyrazol-5-yl]cyclohexyl benzoate.

Workup

  1. temperatureunder heated
  2. temperaturereflux
  3. extractionan organic layer was extracted
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with column chromatography (hexane/ethyl acetate=1:9)

Sources & evidence

ORD record
ord-1939f720342e4e3ab99cb21abb424af7
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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