Dichloromethane → HCID 118277025, compound

HRID 1053707Notes

Reaction equation

HRID 1053707 reaction equation
ClC1C=[C:4](C=CC=1)[C:5]([O:7]O)=O.[Cl:12][CH2:13][CH2:14][N:15](CCCl)[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:40])([CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:18]([CH3:41])[CH:17]=1.[Cl:45]CCl>>[C:36]([O:35][C:33]([NH:32][CH2:31][C:22]([C:19]1[CH:20]=[CH:21][C:16]([N:15]([O:7][CH2:5][CH2:4][Cl:45])[CH2:14][CH2:13][Cl:12])=[CH:17][C:18]=1[CH3:41])([CH3:40])[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:34])([CH3:37])([CH3:39])[CH3:38]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 118277075HCID 118277075, compound

Product 1

HCID 118277025HCID 118277025, compound

Procedure

Adapting literature known protocols (Tercel, et al., J. Med. Chem. 1995, 38, 1247-1252; U.S. Pat. No. 5,602,278; Kirkpatrick, et al., Anti-Cancer Drugs, 1994, 5, 467-472; and U.S. Pat. No. 7,399,785), tert-butyl 4-(tert-butoxycarbonylamino)-3-[4-(2-chloroethoxy(2-chloroethyl)amino)-2-methyl-phenyl]-3-methyl-butanoate (24a) is prepared by adding 3-chloroperoxybenzoic acid (1.42 g, 80 wt-%, 6.6 mmol) to a solution of tert-butyl 3-[4-[bis(2-chloroethyl)amino]-2-methyl-phenyl]-4-(tert-butoxycarbonylamino)-3-methyl-butanoate (7o) (2.52 g, 5.0 mmol) in dichloromethane (DCM) (30 mL) at about room temperature for about 2 h. The reaction is followed by TLC and/or LC/MS till completion. After quenching with a saturated aqueous solution of sodium hydrogencarbonate (NaHCO3), the reaction mixture is extracted with DCM (3×). Further aqueous work-up and purification by silica gel column chromatography yield the title compound (24a).

Workup

  1. custom7,399,785), tert-butyl 4-(tert-butoxycarbonylamino)-3-[4-(2-chloroethoxy(2-chloroethyl)amino)-2-methyl-phenyl]-3-methyl-butanoate (24a) is prepared
  2. customAfter quenching with a saturated aqueous solution of sodium hydrogencarbonate (NaHCO3)
  3. extractionthe reaction mixture is extracted with DCM (3×)
  4. customFurther aqueous work-up and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-11bbd67ff15f4ae5b7ff59308fcba4fe
Source dataset
uspto-grants-2016_07
Patent number
US09394236B2

Reaction notes

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