Chloroform → HCID 21713912, compound

HRID 649810Notes

Reaction equation

HRID 649810 reaction equation
[CH:1]1([C:7]([N:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=3[O:25][CH3:26])[CH2:14][CH2:13]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)Cl.[C:37](Cl)(=[O:39])[CH3:38]>ClCCl>[CH:1]1([C:7]([N:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:37](=[O:39])[CH3:38])=[CH:20][C:19]=3[O:25][CH3:26])[CH2:14][CH2:13]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6367Acetyl chlorideHCID 21713926HCID 21713926, compound

Product 1

HCID 21713912HCID 21713912, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture consisting of 0.35 g of compound of Example 6, 5 mL of chloroform and 0.063 mL of acetyl chloride was stirred for 2.5 h at room temperature, followed by dilution with 50 mL of dichloromethane. The obtained organic phase was then washed with a saturated sodium carbonate solution, and twice with water, followed by drying over anhydrous sodium sulphate and evaporation of the solvents to dryness. The obtained crude product was then purified by flash chromatography (ethyl acetate—3 N solution of ammonia, in methanol; 95:5), and the recovered fraction was evaporated to dryness, affording 0.300 g of the title compound (yield 78%).

Workup

  1. washThe obtained organic phase was then washed with a saturated sodium carbonate solution
  2. dry with materialby drying over anhydrous sodium sulphate and evaporation of the solvents to dryness
  3. customThe obtained crude product
  4. customwas then purified by flash chromatography (ethyl acetate—3 N solution of ammonia, in methanol; 95:5)
  5. customthe recovered fraction was evaporated to dryness

Sources & evidence

ORD record
ord-b55cda5a9ef24017adb6504e0b68d337
Source dataset
uspto-grants-2001_08
Patent number
US06271234B1

Reaction notes

Loading…