Acetic Anhydride → HCID 86612093, compound

HRID 29033Notes

Reaction equation

HRID 29033 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@:11]([CH:14]([O:17][CH3:18])[O:15][CH3:16])([CH3:13])[C@H:10]([OH:19])[C@@H:9]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][C:21]3=[S:29])[C:8]=2[CH:30]=1)([O-:3])=[O:2].[C:31](OC(=O)C)(=[O:33])[CH3:32].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@:11]([CH:14]([O:15][CH3:16])[O:17][CH3:18])([CH3:13])[C@H:10]([O:19][C:31](=[O:33])[CH3:32])[C@@H:9]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][C:21]3=[S:29])[C:8]=2[CH:30]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86612092(2R,3R,4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyran

Product 1

HCID 86612093HCID 86612093, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

200 mg (0.46 mmol) of the compound obtained in Example 1 was dissolved in 2 ml of dichloromethane, to which 87 μl (0.93 mmol) of acetic anhydride, 0.13 ml (0.93 mmol) of triethylamine and 17 mg (0.14 mmol) of 4-dimethylaminopyridine were added in that order. The reaction was stirred for 2 hours at room temperature, 10 ml of saturated NaHCO3 solution was added and extraction was performed with 30 ml of dichloromethane. The extract was washed with brine and dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), to give 211 mg (yield: 97%) of the target compound.

Workup

  1. additionwere added in that order
  2. extractionextraction
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2e61d253854e4125b8ba9b1ecdde84c4
Source dataset
uspto-grants-2008_09
Patent number
US07420060B2

Reaction notes

Loading…