Acetyl chloride → HCID 14835074, compound

HRID 728478Notes

Reaction equation

[CH2:1]([O:17][CH2:18][CH:19]([CH2:29][O:30][CH3:31])[CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH2:27][I:28])(=[O:24])=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:32](Cl)(=[O:34])[CH3:33].C(NC(C)C)(C)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>ClCCl>[C:32]([N:21]([S:22]([CH2:25][CH2:26][CH2:27][I:28])(=[O:24])=[O:23])[CH2:20][CH:19]([CH2:29][O:30][CH3:31])[CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:34])[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled mixture of 0.76 g (1.3 mM) of 1-hexadecyloxy-3-(3-iodopropylsulfonylamino)-2-methoxymethylpropane IIk1 and 0.14 ml (2.0 mM) of acetyl chloride in 10 ml of dichloromethane at 0° C., is added 0.39 ml (2.2 mM) of diisopropylamine and the mixture is stirred at 0° C., for 3 hours. The mixture is poured into ice-water and the product is isolated by dichloromethane extraction. The dichloromethane layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. The residue is purified by column silica gel chromatography using toluene-ethyl acetate (9:1) mixture and 0.81 g (99% yield) of the titled compound IIk1' is obtained.

Workup

washThe dichloromethane layer is washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customevaporated
customThe residue is purified by column silica gel chromatography

Sources & evidence

ORD record: ord-5ce24b3eb4604265b5c7bf8818a92e29
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047540

Reaction notes

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