Acetyl chloride → HCID 67420818, compound

HRID 1037991Notes

Reaction equation

HRID 1037991 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]([CH:20]3[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:45])[N:27]4[CH2:32][CH2:31][N:30]([C:33]5[CH:38]=[CH:37][C:36]([C:39]6[N:44]=[CH:43][CH:42]=[CH:41][N:40]=6)=[CH:35][CH:34]=5)[CH2:29][CH2:28]4)[CH2:21]3)=[O:19])=[CH:14][CH:15]=2)[C:10]([NH2:46])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:47](Cl)(=[O:49])[CH3:48]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]([CH:20]3[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:45])[N:27]4[CH2:28][CH2:29][N:30]([C:33]5[CH:34]=[CH:35][C:36]([C:39]6[N:40]=[CH:41][CH:42]=[CH:43][N:44]=6)=[CH:37][CH:38]=5)[CH2:31][CH2:32]4)[CH2:21]3)=[O:19])=[CH:14][CH:15]=2)[C:10]([NH:46][C:47](=[O:49])[CH3:48])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 67420739HCID 67420739, compound

Product 1

HCID 67420818HCID 67420818, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 36 from Step 1 in CH2Cl2 (0.3 mL) and pyridine (0.3 mL) was added acetyl chloride (50 ul, 0.7 mmol) at rt. The crude was stirred at rt for 30 mins. The crude was quenched with sat. NaHCO3 at rt. The crude was partitioned between EtOAc and H2O. The organic layer was washed with H2O, brine, dried over MgSO4, filtered, and evaporated. The crude was chromatographed to give 20 mg of the product.

Workup

  1. customThe crude was quenched with sat. NaHCO3 at rt
  2. customThe crude was partitioned between EtOAc and H2O
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was chromatographed

Sources & evidence

ORD record
ord-f490c07ead964a59994209a930cc93dd
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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