Chloroacetyl chloride → HCID 68510438, compound

HRID 1868523Notes

Reaction equation

HRID 1868523 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH2:9][NH:10][CH:11]1[CH:15]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:14][N:13]([C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:12]1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[Cl:43][CH2:44][C:45](Cl)=[O:46]>>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH2:9][N:10]([CH:11]1[CH:15]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[CH2:14][N:13]([C:24](=[O:32])[C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[CH2:12]1)[C:45](=[O:46])[CH2:44][Cl:43])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 68509347HCID 68509347, compound

Product 1

HCID 68510438HCID 68510438, compoundYield 58%

Procedure

To a solution of {2-[4-(tert-butyl-dimethyl-silanyloxy)-1-(4-chloro-benzoyl)-pyrrolidin-3-ylamino]-ethyl}-carbamic acid tert-butyl ester (389 mg, 0.78 mmol) at 0° C., was added DIPEA (0.150 mL, 0.85 mmol) and chloroacetyl chloride (62 uL, 0.78 mmol). The reaction mixture was stirred at RT for overnight. The organic phase was washed with Sat. NaHCO3, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (Ethyl acetate:Hexane:1:2) to give the desired product (260 mg, 58% yield) as a colorless oil. MS: (ESI), M/Z, 574 (M+1). Retention time: 2.78 min (FA-polar).

Workup

  1. washThe organic phase was washed with Sat. NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (Ethyl acetate:Hexane:1:2)

Sources & evidence

ORD record
ord-f1056cb479774d0bbcd276613308c95c
Source dataset
uspto-grants-2009_12
Patent number
US07635698B2

Reaction notes

Loading…