Acetic Anhydride → HCID 24821335, compound

HRID 1028464Notes

Reaction equation

HRID 1028464 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([NH:23][C:33](=[O:35])[CH3:34])[CH3:22])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69443896HCID 69443896, compound

Product 1

HCID 24821335HCID 24821335, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1F (0.15 g, 0.0004 mol) and excess triethylamine (2 mL) in methylene chloride (5 mL) was added excess acetic anhydride (1 mL) and the mixture was stirred at room temperature for 15 minutes. After quenching with methanol (5 mL), the solvent was concentrated and the residue was purified on silica gel (50˜75% ethyl acetate in hexane) to give 0.12 g of the title compound (76% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=6.25 Hz, 6 H) 1.49 (d, J=6.99 Hz, 3 H) 2.00 (s, 3 H) 4.44-4.60 (m, 1 H) 5.06-5.20 (m, 1 H) 5.67 (d, J=6.99 Hz, 1 H) 6.87-6.97 (m, 2 H) 7.16-7.24 (m, 2 H) 7.27-7.34 (m, 2 H) 7.37 (s, 1 H) 7.38-7.44 (m, 2 H). MS (ESI), m/z 396.9 (M+H)+.

Workup

  1. customAfter quenching with methanol (5 mL)
  2. concentrationthe solvent was concentrated
  3. customthe residue was purified on silica gel (50˜75% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b9bbf0e13efa442c888db017956231b7
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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