2-Acetamino-3-oxooctadecanoic acid → N-(1,3-dihydroxyoctadecan-2-yl)acetamide

HRID 1416805Notes

Reaction equation

HRID 1416805 reaction equation
[NH:1]([CH:5]([C:9](=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:6](O)=[O:7])[C:2]([CH3:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[NH:1]([CH:5]([CH:9]([OH:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][OH:7])[C:2]([CH3:4])=[O:3]

Participants

3

Reactant 2

HCID 186251832-Acetamino-3-oxooctadecanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2506N-(1,3-dihydroxyoctadecan-2-yl)acetamide

Procedure

As shown below, the ester and ketone groups in an ester of 2-acetamino-3-oxooctadecanoic acid are reduced in the presence of lithium aluminium hydride (referred to as LAH) to obtain a racemate of 2-acetaminooctadecane-1,3-diol, as follows: ##STR7##

Sources & evidence

ORD record
ord-fc484f13a60d49f0b2093d8639ec0a45
Source dataset
uspto-grants-1999_06
Patent number
US05916578

Reaction notes

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