HCID 10602365, compound → HCID 10790794, compound

HRID 1645785Notes

Reaction equation

HRID 1645785 reaction equation
C([O:5][C:6]([CH2:8][N:9]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:10]([CH:12]([CH2:19][S:20]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)(=[O:22])=[O:21])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:11])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[CH3:18][O:17][C:15]([CH2:14][CH2:13][CH:12]([CH2:19][S:20]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)(=[O:21])=[O:22])[C:10]([N:9]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:8][C:6]([OH:7])=[O:5])=[O:11])=[O:16]

Participants

3

Reactant 1

HCID 10602365HCID 10602365, compound

Product 1

HCID 10790794HCID 10790794, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl 4-(N-tert-butoxycarbonylmethyl-N-pentylcarbamoyl)-5-(2-naphthylsulfonyl)pentanoate (0.47 g) was dissolved in trifluoroacetic acid (5 ml) at 0° C., and stirred at room temperature for 2 hours. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash column chromatography on silica eluting with chloroform/methanol (15:1) to give 0.34 g of N-[2-(2-methoxycarbonylethyl)-3-(2-naphthylsulfonyl)propionyl]-N-pentylglycine as an amorphous solid. ##STR18##

Workup

  1. concentrationAfter the reaction mixture was concentrated in vacuo
  2. customthe resulting residue was purified by flash column chromatography on silica eluting with chloroform/methanol (15:1)

Sources & evidence

ORD record
ord-55a0ab1ef7604c9ebbc4dfe2dcfb67c5
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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