Chloroacetyl chloride → N-benzyl-2-chloro-N-((2R,3R)-2-hydroxypentan-3-yl)acetamide

HRID 81159Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([NH:15][C@H:16]([CH2:20][CH3:21])[C@H:17]([OH:19])[CH3:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:22][CH2:23][C:24](Cl)=[O:25]>ClCCl>[CH2:8]([N:15]([C@H:16]([CH2:20][CH3:21])[C@H:17]([OH:19])[CH3:18])[C:24](=[O:25])[CH2:23][Cl:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -40 °C

Procedure

Triethylamine (0.43 mL, 3.4 mmol) was added to a −40° C. solution of (2R,3R)-3-(benzylamino)pentan-2-ol (220 mg, 1.1 mmol) in dichloromethane (100 mL), followed by the addition of 2-chloroacetyl chloride (0.10 mL, 1.1 mmol) dropwise. The reaction mixture was stirred at −40° C. for 1 hour and then quenched with saturated NaHCO3 solution. The layers were separated, and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue on a silica gel column (0 to 50% EtOAc/hexanes) afforded N-benzyl-2-chloro-N-((2R,3R)-2-hydroxypentan-3-yl)acetamide. MS APCl calc'd for C14H20ClNO2 [M+H]+ 270. found 270.

Workup

customquenched with saturated NaHCO3 solution
customThe layers were separated
extractionthe aqueous layer was extracted with dichloromethane (3×10 mL)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue on a silica gel column (0 to 50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-6a5df74267484998a9689d2c3c05eb2b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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