Acetyl chloride → HCID 70034980, compound

HRID 411254Notes

Reaction equation

HRID 411254 reaction equation
[NH2:1][C@H:2]([CH3:24])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=2)[CH2:7][CH2:6]1)=[O:4].[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][CH2:11][N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C@H:2]([NH:1][C:25](=[O:27])[CH3:26])[CH3:24])[CH2:6][CH2:7]2)=[CH:20][CH:19]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 70033449HCID 70033449, compound

Product 1

HCID 70034980HCID 70034980, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of Example 29 (1 mmol) and TEA (1.1 mmol) in dichloromethane (10 mL) was treated with acetyl chloride (1 mmol). After stirring for four hours at 0° C., the reaction mixture was quenched with water and extracted with dichloromethane. The combined dichloromethane layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was purified through silica gel chromatography to afford the desired product in 83% yield.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined dichloromethane layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified through silica gel chromatography

Sources & evidence

ORD record
ord-481241fe2d2b4513ac5e2c3910993011
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

Loading…