Acetyl chloride → HCID 86717460, compound

HRID 712000Notes

Reaction equation

HRID 712000 reaction equation
[OH:1][CH2:2][CH:3]([O:6][CH2:7][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[CH2:10])[CH:4]=[CH2:5].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)Cl>[C:26]([O:1][CH2:2][CH:3]([O:6][CH2:7][C@@H:8]([NH:11][C:12]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:18])[CH:9]=[CH2:10])[CH:4]=[CH2:5])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86717459HCID 86717459, compound

Product 1

HCID 86717460HCID 86717460, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of tert-butyl [(1S)-1-({[1-(hydroxymethyl)prop-2-en-1-yl]oxy}methyl)prop-2-en-1-yl]carbamate (268 mg, 1.04 mmol) in methylene chloride (10 mL) was added with triethylamine (435 μL, 3.12 mmol). The mixture was cooled to 0° C., and acetyl chloride (150 μL, 2.1 mmol) was added drop wise. The reaction was stirred at room temperature for 2 h, then quenched with water. The organic layer was concentrated and the resultant residue purified on silica gel (eluting with 20% ethyl acetate/hexanes) to give the desired product (0.26 g, 85%). LCMS calculated for C10H18NO3 (M−100+H)+: m/z=200.1. Found: 200.1.

Workup

  1. customquenched with water
  2. concentrationThe organic layer was concentrated
  3. customthe resultant residue purified on silica gel (eluting with 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0a9d788a7da74c6688e056d5cf3de7bd
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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