Acetic Anhydride → HCID 67357344, compound

HRID 889439Notes

Reaction equation

HRID 889439 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12].[C:20]([O:23][C:24](=O)C)(=[O:22])C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][N:16]1[CH2:17][CH2:18][N:13]([C:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[NH:1][C:20](=[O:22])[O:23][CH3:24])=[O:12])[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 59313927HCID 59313927, compound

Product 1

HCID 67357344HCID 67357344, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 69B (540 mg, 2.04 mmol) in DCM (20 mL) was added TEA (0.570 mL, 4.09 mmol), acetic anhydride (0.289 mL, 3.06 mmol), and DMAP (2 mg, 0.016 mmol). The reaction mixture was stirred overnight, then washed with saturated aqueous NaHCO3, dried, and concentrated. The reaction mixture was purified by flash chromatography, (SiO2, 24 g, 0-10% MeOH/DCM) to give Intermediate 69C (600 mg, 96%) as a yellow solid. HPLC: Rt=0.517 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). MS (ES): m/z=307 [M+H]+.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. customThe reaction mixture was purified by flash chromatography, (SiO2, 24 g, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-27d98686fd7a4195970f8c6005f18ae5
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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