Acetic Anhydride → HCID 86585978, compound

HRID 1016265Notes

Reaction equation

HRID 1016265 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:27])[C:17](=[CH:28][O:29][CH2:30][CH3:31])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[C:32]([O:27][C@H:18]1[C:17](=[CH:28][O:29][CH2:30][CH3:31])[CH2:16][C@H:15]2[C@H:14]3[C@H:23]([CH2:22][CH2:21][C@:19]12[CH3:20])[C:24]1[CH:25]=[CH:26][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[CH2:12][CH2:13]3)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 70116396HCID 70116396, compound

Product 1

HCID 86585978HCID 86585978, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3 (194 mg), acetic anhydride (1 mL) in pyridine (3ml) was stirred at rt overnight under N2. Reaction was poured into saturated aqueous NaHCO3 (150 mL) and extracted with CH2Cl2 (3×, 100 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification of the residue by flash chromatography on a 2×20 cm column of silica gel using hexanes/EtOAc (4:1) as eluent gave 183 mg (86%) of 4 as a white solid: TLC, T-2, Rf0.67.

Workup

  1. customReaction
  2. extractionextracted with CH2Cl2 (3×, 100 mL)
  3. dry with materialCombined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography on a 2×20 cm column of silica gel

Sources & evidence

ORD record
ord-d5c3aab95a5b41d7a2d36a6aef1b6881
Source dataset
uspto-grants-2002_11
Patent number
US06476012B2

Reaction notes

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