Acetyl chloride → HCID 18539964, compound

HRID 411252Notes

Reaction equation

HRID 411252 reaction equation
[NH2:1][C:2](=[N:26][OH:27])[C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>CC(C)=O>[C:35]([O:27][NH:26][CH:2]([NH2:1])[C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)=[CH:5][CH:4]=1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 91380196HCID 91380196, compound

Product 1

HCID 18539964HCID 18539964, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of Example 2C (0.11 g, 0.29 mmol) and triethylamine (400 μL, 2.9 mmol) in acetone (10 mL) was treated with a solution of acetyl chloride (200 μL, 2.8 mmol) in acetone (1 mL) over 30 minutes, stirred for 1 hour, and concentrated. The concentrate was partitioned between water and dichloromethane. The layers were separated, and the aqueous layer was extracted with dichloromethane. The combined extracts were dried (Na2SO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel using 95:5 dichloromethane:methanol to afford 106 mg (87%) of the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was partitioned between water and dichloromethane
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by column chromatography on silica gel using 95:5 dichloromethane

Sources & evidence

ORD record
ord-0bcbe360b04b4dd5b9e67ca9143012cb
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

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