Sodium Azide → HCID 19986056, compound

HRID 974681Notes

Reaction equation

HRID 974681 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:41])[O:9][CH2:10][CH:11]([O:34][C:35]1[CH:39]=[C:38]([CH3:40])[O:37][N:36]=1)[CH2:12][O:13][C:14]1[CH:18]=[C:17]([CH2:19][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][CH3:33])[O:16][N:15]=1.[N-:42]=[N+:43]=[N-:44].[Na+].[CH:46]([O-])([O-])OCC>C(O)(=O)C>[N:1]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:41])[O:9][CH2:10][CH:11]([O:34][C:35]2[CH:39]=[C:38]([CH3:40])[O:37][N:36]=2)[CH2:12][O:13][C:14]2[CH:18]=[C:17]([CH2:19][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][CH3:33])[O:16][N:15]=2)[CH:46]=[N:44][N:43]=[N:42]1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 53630039EthylorthoformateHCID 54444491HCID 54444491, compound

Product 1

HCID 19986056HCID 19986056, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.230 g of (2RS)-2-(5-methyl-3-isoxazolyloxy)-3-(5-pentadecyl-3-isoxazolyloxy)propyl N-(5-aminopentyl)carbamate (prepared as described in Example 27), 0.067 g of sodium azide, 0.30 ml of ethyl orthoformate and 0.45 ml of acetic acid was heated on an oil bath kept at 115° C. for 3 hours. The solvent was removed by evaporation under reduced pressure, and then the residue was subjected to column chromatography through 10 g of silica gel. 0.152 g of the title compound was obtained as a powder from the fractions eluted with mixtures of methylene chloride and methanol ranging from 5:1 to 2:1 by volume. It melted at 82°-84° C. (after reprecipitation from a mixture of methylene chloride and diethyl ether).

Workup

  1. temperaturewas heated on an oil bath
  2. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-84ed7363514f4f6cb634576d6771edf3
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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