Acetic Anhydride → HCID 131728679, compound

HRID 1363387Notes

Reaction equation

HRID 1363387 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][C@H:24]1[OH:30].[C:31](OC(=O)C)(=[O:33])[CH3:32].CN(C1C=CC=CN=1)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][C@H:24]1[O:30][C:31](=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 218852-DimethylaminopyridineHCID 131728666HCID 131728666, compound

Product 1

HCID 131728679HCID 131728679, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound of example 106 (3.35 g, 7.79 mmol) in dry CHCl3 (25 mL) was added acetic anhydride (1.76 g, 17.43 mmol) at 25° C. with stirring, followed by the addition of dimethylaminopyridine (0.033 g, 1% w/w). The mixture was stirred for 0.5 h. It was poured into ice water (50 mL), basified using a saturated aqueous Na2CO3 solution and extracted using CHCl3 (3×100 mL). The organic extract was washed with water, dried (anhydrous Na2SO4) and concentrated. The oil obtained was purified using a silica gel column and 0.1% MeOH+1% liquor NH3 in CHCl3 as eluant to get the title compound.

Workup

  1. stirringThe mixture was stirred for 0.5 h
  2. extractionextracted
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. customThe oil obtained
  8. customwas purified

Sources & evidence

ORD record
ord-779ac3a3d1bf412790d26605b3b43a7a
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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