Acetic-formic anhydride → HCID 10109317, compound

HRID 1978028Notes

Reaction equation

HRID 1978028 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH:19]([NH:22][OH:23])[CH2:20][CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:24](OC=O)(=[O:26])C>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH:19]([N:22]([OH:23])[CH:24]=[O:26])[CH2:20][CH3:21])(=[O:16])=[O:17])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 21700297HCID 21700297, compound

Product 1

HCID 10109317HCID 10109317, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 75C (0.24 g, 0.72 mmol) in THF (30mL) cooled to 0° C. was treated with formic acetic anhydride (64 mg, 0.72 mmol), stirred for 2 hours, partitioned between water and dichloromethane, dried (Mg2SO4), filtered, and concentrated to afford 0.25 g of crude product which was recrystallized in ethyl acetate to provide 106 mg (41%) of the desired product.

Workup

  1. custompartitioned between water and dichloromethane
  2. dry with materialdried (Mg2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford 0.25 g of crude product which
  6. customwas recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-37ac91eb20ef459f923207c2a0f228f9
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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