Dichloromethane → HCID 77750055, compound

HRID 840703Notes

Reaction equation

HRID 840703 reaction equation
Cl[C:2]1[CH:3]=C(C=C[CH:11]=1)C(OO)=O.[CH2:12]([NH:14][C:15]([CH:17]1[CH2:21][CH:20]([N:22]2[C:26]3[N:27]=[C:28]([S:41]CCC)[N:29]=[C:30]([NH:31][CH:32]4[CH2:34][CH:33]4[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:25]=3[N:24]=[N:23]2)[CH:19]([OH:45])[CH:18]1[OH:46])=[O:16])[CH3:13].ClCCl>C(O)C>[CH2:12]([NH:14][C:15]([CH:17]1[CH2:21][CH:20]([N:22]2[C:26]3[N:27]=[C:28]([S:41][CH:2]([CH3:3])[CH3:11])[N:29]=[C:30]([NH:31][CH:32]4[CH2:34][CH:33]4[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:25]=3[N:24]=[N:23]2)[CH:19]([OH:45])[CH:18]1[OH:46])=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 77750217HCID 77750217, compound

Product 1

HCID 77750055HCID 77750055, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloroperoxybenzoic acid (50%, 9.0 g) was added to a suspension of the product of example 1, step e) (4.1 g) in ethanol (200 ml) and dichloromethane (50 ml) and the resulting solution stirred at room temperature for 18 hours. The reaction mixture was concentrated and the residue taken up in ethyl acetate (500 ml) , washed with 10% aqueous sodium metabisulfite solution (2×100 ml) and 10% aqueous sodium bicarbonate solution (2×100 ml) then dried and concentrated. Purification (SiO2, ethyl acetate as eluant) gave the subtitle compound (2.4 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with 10% aqueous sodium metabisulfite solution (2×100 ml) and 10% aqueous sodium bicarbonate solution (2×100 ml)
  3. customthen dried
  4. concentrationconcentrated
  5. customPurification (SiO2, ethyl acetate as eluant)

Sources & evidence

ORD record
ord-cffd2b68f6f44210b2df3e8320e7d484
Source dataset
uspto-grants-2002_04
Patent number
US06369064B1

Reaction notes

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