Chloroacetyl chloride → HCID 86725425, compound

HRID 1525889Notes

Reaction equation

HRID 1525889 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([NH:13][CH2:14][C:15]2([OH:28])[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:38][CH2:39][C:40](Cl)=[O:41]>ClCCl.C(=O)(O)[O-].[Na+]>[Si:1]([O:8][CH2:9][C:10]1([N:13]([CH2:14][C:15]2([OH:28])[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)[C:40](=[O:41])[CH2:39][Cl:38])[CH2:11][CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 71270895HCID 71270895, compound

Product 1

HCID 86725425HCID 86725425, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirring solution of tert-butyl 4-(((1-(((tert-butyldimethylsilyl)oxy)methyl)cyclopropyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate (1.688 mmol) and N,N-diisopropylethylamine (4.22 mmol) in anhydrous dichloromethane (30 mL) cooled to 0° C. was added neat chloroacetyl chloride (2.53 mmol). After 30 min, the reaction was diluted with saturated aq sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and were evaporated onto silica. Purification of the solid by flash chromatography (30% ethyl acetate in hexanes) afforded the title product (742 mg, 85% yield) as a light orange oil. MS(ES)+ m/e 491.4 [M+H]+.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customwere evaporated onto silica
  4. customPurification of the solid by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-875581ba79634872badfe263650ba641
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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