Acetic Anhydride → HCID 69926998, compound

HRID 1421684Notes

Reaction equation

HRID 1421684 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C@@H:17]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)[CH:26]=3)[CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40].CCOC(C)=O>N1C=CC=CC=1>[ClH:1].[C:39]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([C@@H:17]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)[CH:26]=3)[CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 21969138HCID 21969138, compound

Product 1

HCID 69926998HCID 69926998, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the free base of compound of Example 7 (322 mg, 0.67 mmol) in pyridine (10 ml) was heated with acetic anhydride (126 μl) and the mixture stirred at RT for 24 h. The solvent was removed in vacuo, the residue azeotroped twice with toluene and partitioned between aqueous NaOH (pH 13) and EtOAc. The aqueous layer was further extracted with EtOAc and the combined organic layer dried (Na2SO4) then concentrated in vacuo to give an off-white glass. Chromatography (SiO2 ; EtOAc) afforded the title compound free base (303.6 mg) as an off-white glass.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped twice with toluene
  3. custompartitioned between aqueous NaOH (pH 13) and EtOAc
  4. extractionThe aqueous layer was further extracted with EtOAc
  5. dry with materialthe combined organic layer dried (Na2SO4)
  6. concentrationthen concentrated in vacuo
  7. customto give an off-white glass

Sources & evidence

ORD record
ord-c38cdd6968e64f0aadf4d2522214a585
Source dataset
uspto-grants-2000_06
Patent number
US06077854

Reaction notes

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