Acetic Anhydride → HCID 19986057, compound

HRID 974682Notes

Reaction equation

HRID 974682 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:42])[O:10][CH2:11][CH:12]([O:36][C:37]1[CH:41]=[CH:40][O:39][N:38]=1)[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[O:17][N:16]=1.[C:43](OC(=O)C)(=[O:45])[CH3:44]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[C:43]([N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:9](=[O:42])[O:10][CH2:11][CH:12]([O:36][C:37]1[CH:41]=[CH:40][O:39][N:38]=1)[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[O:17][N:16]=1)(=[O:45])[CH3:44]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 19986067HCID 19986067, compound

Product 1

HCID 19986057HCID 19986057, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

0.370 g of (2RS)-3-(5-hexadecyl-3-isoxazolyloxy)-2-(3-isoxazolyloxy)propyl N-(2-pyridylmethyl)carbamate (prepared as described in Example 30), 0.60 ml of acetic anhydride and 0.733 g of 4-(N,N-dimethylamino)pyridine were dissolved in 10 ml of toluene, and the mixture was stirred on an oil bath kept at 90° C. for 48 hours. The solvent was distilled off, and the residue was purified by column chromatography through 15 g of silica gel and by medium pressure liquid chromatography using a Lobar B column, 0.308 g of the title compound was obtained, as an oil, from the fractions eluted with methylene chloride.

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was purified by column chromatography through 15 g of silica gel and by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-339c385ab6ec40d187a03d882ad6a051
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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