Acetyl chloride → HCID 71607551, compound

HRID 1405639Notes

Reaction equation

HRID 1405639 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(O)=O.[CH3:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH2:20][CH2:21][NH:22][CH2:23][C@H:24]2[O:28][C:27](=[O:29])[N:26]([C:30]3[CH:31]=[CH:32][C:33]4[S:34][CH2:35][C:36](=[O:40])[NH:37][C:38]=4[N:39]=3)[CH2:25]2)[C:10]1=[O:41]>CN(C=O)C.CCOCC>[CH3:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH2:20][CH2:21][N:22]([CH2:23][C@H:24]2[O:28][C:27](=[O:29])[N:26]([C:30]3[CH:31]=[CH:32][C:33]4[S:34][CH2:35][C:36](=[O:40])[NH:37][C:38]=4[N:39]=3)[CH2:25]2)[C:1](=[O:3])[CH3:2])[C:10]1=[O:41]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 90216296HCID 90216296, compound

Product 1

HCID 71607551HCID 71607551, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Acetyl chloride (0.009 ml) was added to a solution of the compound of Example 55 (56 mg) and TEA (0.017 ml) in DMF (2 ml). The mixture was stirred at rt overnight. The reaction mixture was partitioned between water and EA/MeOH 9:1. The aq. layer was extracted with EA/MeOH 9:1 and the combined org. layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting material was purified by CC (EA/MeOH 19:1) and afforded, after stirring in ether, a slightly yellow solid (175 mg; 42% yield).

Workup

  1. customThe reaction mixture was partitioned between water and EA/MeOH 9:1
  2. extractionThe aq. layer was extracted with EA/MeOH 9:1
  3. washlayers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material was purified by CC (EA/MeOH 19:1)
  8. customafforded

Sources & evidence

ORD record
ord-590b53d720b6447aaab2f103509626e5
Source dataset
uspto-grants-2014_12
Patent number
US08916573B2

Reaction notes

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