Dichloromethane → HCID 118276581, compound

HRID 1053667Notes

Reaction equation

HRID 1053667 reaction equation
ClC1C=[C:4](C=CC=1)[C:5]([O:7]O)=O.ClCC[N:15]([CH2:41][CH2:42][Cl:43])[C:16]1[CH:17]=[CH:18][C:19]([CH3:40])=[C:20]([CH2:22][C@@H:23]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:21]=1.[Cl:44]CCl>>[C:36]([O:35][C:33]([NH:32][C@H:23]([CH2:22][C:20]1[CH:21]=[C:16]([N:15]([O:7][CH2:5][CH2:4][Cl:44])[CH2:41][CH2:42][Cl:43])[CH:17]=[CH:18][C:19]=1[CH3:40])[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])=[O:34])([CH3:38])([CH3:39])[CH3:37]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 118276572HCID 118276572, compound

Product 1

HCID 118276581HCID 118276581, compound

Procedure

Adapting literature known protocols (Tercel, et al., J. Med. Chem. 1995, 38, 1247-1252; Kirkpatrick, U.S. Pat. No. 5,602,278; Kirkpatrick, et al., Anti-Cancer Drugs, 1994, 5, 467-472; and Kirkpatrick, et al., U.S. Pat. No. 7,399,785), tert-butyl(3R)-3-(tert-butoxycarbonylamino)-4-[5-(2-chloroethoxy(2-chloroethyl)amino)-2-methyl-phenyl]butanoate (21a) is prepared by adding 3-chloroperoxybenzoic acid (1.42 g, 80 wt-%, 6.6 mmol) to a solution of tert-butyl(3R)-4-[5-[bis(2-chloroethyl)amino]-2-methyl-phenyl]-3-(tert-butoxycarbonylamino)butanoate (6e) (2.43 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 to 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 (21a).

Workup

  1. custom7,399,785), tert-butyl(3R)-3-(tert-butoxycarbonylamino)-4-[5-(2-chloroethoxy(2-chloroethyl)amino)-2-methyl-phenyl]butanoate (21a) 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-dfd57d7f3b4a4b2faa20b673461ed57f
Source dataset
uspto-grants-2016_07
Patent number
US09394237B2

Reaction notes

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