Acetic Anhydride → HCID 70084326, compound

HRID 399434Notes

Reaction equation

HRID 399434 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10](=[O:42])[C@@H:11]([NH2:41])[CH2:12][NH:13][C:14]([C:16]1[CH:40]=[C:19]2[C:20](=[O:39])[N:21]([CH2:24][CH2:25][CH:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)[CH2:22][CH2:23][N:18]2[N:17]=1)=[O:15]>C1COCC1>[CH3:8][O:9][C:10](=[O:42])[C@@H:11]([NH:41][C:1](=[O:3])[CH3:2])[CH2:12][NH:13][C:14]([C:16]1[CH:40]=[C:19]2[C:20](=[O:39])[N:21]([CH2:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]3)[CH2:22][CH2:23][N:18]2[N:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18665861HCID 18665861, compound

Product 1

HCID 70084326HCID 70084326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (70 ml, 0.76 mmol), was added to a cooled (0°) solution of 4-3 (350 mg, 0.69 mmol) in 10 ml THF. The resulting solution was allowed to warm to room temperature and stirred for 18 h, then concentrated, and the residue was dissolved in 50 ml ethyl acetate and washed successively with NaHCO3, H2O, 10% KHSO4, H2 O, and brine (25 ml each). The organic layer was dried over Na2 SO4 and evaporated giving a colorless residue which was chromatographed on silica gel with 3% CH3OH/CH2Cl2 to yield 4-4 as a white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in 50 ml ethyl acetate
  3. washwashed successively with NaHCO3, H2O, 10% KHSO4, H2 O, and brine (25 ml each)
  4. customThe organic layer was dried over Na2 SO4
  5. customevaporated
  6. customgiving a colorless residue which
  7. customwas chromatographed on silica gel with 3% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-3f18fee048dc4a9091e5791a441a1a88
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

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