Water → 1-[(1-Hydroxy-naphthalene-2-carbonyl)-amino]-cyclopentanecarboxylic acid methyl ester

HRID 2062113Notes

Reaction equation

HRID 2062113 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:11])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[OH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C)C=O>[CH3:2][O:3][C:4]([C:6]1([NH:11][C:23]([C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]=2[OH:12])=[O:24])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 68441-Hydroxy-2-naphthoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HCl

Product 1

HCID 583701211-[(1-Hydroxy-naphthalene-2-carbonyl)-amino]-cyclopentanecarboxylic acid methyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g 1-amino-cyclopentanecarboxylic acid methyl ester hydrochloride, 0.698 g 1-hydroxy-2-naphthoic acid, 2.12 g HATU and 1.94 ml N,N′diisopropyl-ethylamine in 40 ml of dimethylformamide were stirred at 65° C. for 1 hour, followed by room temperature for 2 days. Water was added and the mixture was extracted with diethyl ether three times. The combined organic layers were dried with magnesium sulfate and concentrated in vacuo. Purification by flash chromatography on silica with heptane/ethyl acetate afforded 0.5 g of 1-[(1-Hydroxy-naphthalene-2-carbonyl)-amino]-cyclopentanecarboxylic acid methyl ester.

Workup

  1. extractionthe mixture was extracted with diethyl ether three times
  2. dry with materialThe combined organic layers were dried with magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica with heptane/ethyl acetate

Sources & evidence

ORD record
ord-01d4f52d2d6140888dbc2ed153171494
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

Loading…