Hydrochloric Acid → HCID 59261037, compound

HRID 643547Notes

Reaction equation

HRID 643547 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:14]1([C:20]([N:22]2[CH2:27][C:26]3[CH:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[CH:30]=[CH:31][C:25]=3[O:24][CH2:23]2)=[O:21])[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]1)[CH3:13].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:12]([C:14]1([C:20]([N:22]2[CH2:27][C:26]3[CH:28]=[C:29]([C:32]([F:34])([F:35])[F:33])[CH:30]=[CH:31][C:25]=3[O:24][CH2:23]2)=[O:21])[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]1)(=[O:11])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59261074HCID 59261074, compound

Product 1

HCID 59261037HCID 59261037, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A precooled (−78° C.) solution of oxalyl chloride (2.82 mL, 32.4 mmol) in 150 mL of DCM was treated dropwise with a solution of DMSO (4.60 mL, 64.8 mmol) in 25 mL of DCM. After an additional 5 min, a solution of 3-(1-hydroxyethyl)-3-{[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentanol (4.33 g, 10.8 mmol) in 25 mL of DCM was added dropwise. The reaction mixture was stirred for an additional 30 min, then neat triethylamine (18.1 mL, 130 mmol) was added dropwise. The mixture was stirred for an additional 10 min, then was warmed to rt and stirred for 1.5 h. The reaction mixture was poured into 1N HCl solution and the resulting mixture was extracted with DCM. The organic layer was washed again with 1N HCl solution, then with saturated NaHCO3 solution, and finally with brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by MPLC (silica, 75% ethyl acetate/hexanes) gave 3-acetyl-3-{[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentanone as a mixture of two enantiomers. ESI-MS calc. for C17H16F3NO4: 355; Found: 356 (M+).

Workup

  1. stirringThe mixture was stirred for an additional 10 min
  2. stirringstirred for 1.5 h
  3. extractionthe resulting mixture was extracted with DCM
  4. washThe organic layer was washed again with 1N HCl solution
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by MPLC (silica, 75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1ef2028519714984919f6bdee0a3a158
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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