Sodium Carbonate → HCID 57246710, compound

HRID 1920604Notes

Reaction equation

HRID 1920604 reaction equation
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].Br[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17](OC)=[CH:16][CH:15]=1)=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O>[CH2:13]([O:12][C:10]([CH2:9][S:4][CH2:3][C@@H:2]([C:5]([OH:7])=[O:6])[NH2:1])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 92851D-CysteineHCID 132332344-Methoxybenzyl 2-bromoacetate

Product 1

HCID 57246710HCID 57246710, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

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 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-996c396e5ffb46a187e68aa61afd4c98
Source dataset
uspto-grants-2012_05
Patent number
US08173133B2

Reaction notes

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