Acetyl chloride → HCID 23648637, compound

HRID 404883Notes

Reaction equation

HRID 404883 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([CH:21]([NH2:23])[CH3:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[C:26](Cl)(=[O:28])[CH3:27]>O1CCCC1.C(N(CC)CC)C.ClC(Cl)C>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([CH:21]([NH:23][C:26](=[O:28])[CH3:27])[CH3:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 69435781HCID 69435781, compound

Product 1

HCID 23648637HCID 23648637, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of Example 17F (600 mg, 1.79 mmol) in tetrahydrofuran (5 mL) and triethyl amine (1.0 mL) was cooled to 0° C. To this was added acetyl chloride (300 μL, 4.22 mmol) at 0° C. The mixture was stirred at room temperature for 30 minutes. The reaction was diluted with dichloroethane, which was washed with water and concentrated. The residue was purified on silica gel eluting with hexane and ethyl acetate gradient to give the desired product as a white solid (500 mg, 77%). MS (DCI): m/z 381 (M+H); 1H NMR (300 MHz, CDCl3) δ ppm 7.66-7.76 (m, 2H), 6.95-7.04 (m, 4H), 6.86-6.93 (m, 2H), 6.40 (s, 1H), 5.82 (d, J=8.46 Hz, 1H), 5.32-5.47 (m, 1H), 4.43-4.59 (m, 1H), 2.04 (s, 3H), 1.58 (d, J=6.99 Hz, 3H), 1.35 (d, J=6.25 Hz, 6H).

Workup

  1. washwas washed with water
  2. concentrationconcentrated
  3. customThe residue was purified on silica gel eluting with hexane and ethyl acetate gradient

Sources & evidence

ORD record
ord-c79206388a34451aa5ad5b1c747abc1d
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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