(r)-3-Tetradecanoyloxytetradecanoic acid chloride → (2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol

HRID 1714754Notes

Reaction equation

HRID 1714754 reaction equation
[C:1]([O:16][C@H:17]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:18][C:19](Cl)=[O:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]CCCCCCC.[NH2:33][CH2:34][CH2:35][CH2:36][C@@H:37]([NH:41]C(=O)C[C@H](O)CCCCCCCCCCC)[CH:38](N)[OH:39]>>[NH2:33][CH2:34][CH2:35][CH2:36][C@@H:37]([NH:41][C:19](=[O:20])[CH2:18][C@H:17]([O:16][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:38][OH:39]

Participants

3

Reactant 2

HCID 87421468(r)-3-Tetradecanoyloxytetradecanoic acid chlorideHCID 87421561(2r)-5-Amino-2-[(r)-3-hydroxytetradecanoylamino]pentan-1-ol amine

Product 1

HCID 11476040(2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol

Procedure

D-cysteine is S-alkyl substituted with p-methoxybenzyl bromoacetate in presence of sodium carbonate in a THF-water medium. The S-benzyloxycarbonylmethylcysteine thus obtained is N-acylated with (R)-3-tetradecanoyloxytetradecanoic acid chloride, and the S-alkyl-N-acyl-D-cysteine derivative is then coupled with (2R)-5-amino-2-[(R)-3-hydroxytetradecanoylamino]pentan-1-ol amine {obtained by hydrogenolysis of the (2R)-5-amino-2-[(R)-3-benzyloxy-tetradecanoyl-amino]pentan-1-ol, see 4.1.1.} in presence of IIDQ. The thus obtained product is selectively O-acylated in its primary position with the ester derived from reacting HOBt with 7-(p-methoxybenzyloxy-carbonylamino)heptanoic acid. The two p-methoxybenzyl groups are then removed by treating the ester with aqueous trifluoroacetic acid. C59H112N4O10S. MM 1069.64.

Sources & evidence

ORD record
ord-2c49e7941d6847b7a746d1d1ed18bf01
Source dataset
uspto-grants-2010_09
Patent number
US07799762B2

Reaction notes

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