Acetic Acid → HCID 10996063, compound

HRID 1596048Notes

Reaction equation

HRID 1596048 reaction equation
[F:1][C:2]([F:39])([F:38])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]=3[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[H-].[Na+].[CH2:42]([O:49][C:50](Cl)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CC(O)=O>CN(C=O)C>[F:39][C:2]([F:1])([F:38])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([S:16]([N:19]([CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]=3[C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[C:50]([O:49][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:51])(=[O:18])=[O:17])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 10864624HCID 10864624, compound

Product 1

HCID 10996063HCID 10996063, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 9E (1.255 g, 2.25 mmol) in DMF (20 mL) under N2 at 0° C. was treated with NaH (60% dispersion in mineral oil, 180 mg, 4.50 mmol) and allowed to stirr for 30 minutes. Benzylchloroformate (0.68 mL, 4.50 mmol) was added, the mixture was allowed to stir for 2 hours, and HOAc was added. The solvent was removed and the residue was dissolved in ethyl acetate (100 mL), washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. Purification over silica gel with 30% hexanes/CH2Cl2 provided 1.19 g (77%) of the desired compound as a white solid.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification over silica gel with 30% hexanes/CH2Cl2

Sources & evidence

ORD record
ord-47e9bfea17f6461c9b0a7e1120a59dc2
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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