Hydrochloric Acid → HCID 23365837, compound

HRID 1723239Notes

Reaction equation

HRID 1723239 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[C:6]([CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=2[O:24][CH3:25])=[CH:5]1)(=[O:3])[CH3:2].[CH:26]1([CH2:31][C:32](O)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:32](=[O:33])[CH2:31][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:10][CH:11]=2)[C:6]([CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=2[O:24][CH3:25])=[CH:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 71606Cyclopentylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23365881HCID 23365881, compound

Product 1

HCID 23365837HCID 23365837, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(1-acetyl-5-aminoindol-3-ylmethyl)-3-methoxybenzoic acid (Z) (0.31 g.), cyclopentylacetic acid (0.117 g.), 4-(dimethylamino)pyridine (0.233 g.) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.35 g.) in dichloromethane (20 ml.), under a nitrogen atmosphere, was stirred at ambient temperature for two hours. The mixture was acidified with hydrochloric acid (1N, 30 ml.), extracted with ethyl acetate (3×50 ml.), and the combined extracts dried (MgSO4) and evaporated. The residual oil was purified by flash chromatography on silica gel (100 ml.), eluting with 50:45:5 v/v/v hexane:dichloromethane:ethyl acetate, to give a product which was recrystallized from a mixture of tetrahydrofuran and ether, and then from a mixture of ethanol and water, to give the title compound (0.055 g., 14%), as a white solid, m.p. .245°-247° C.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml.)
  2. dry with materialthe combined extracts dried (MgSO4)
  3. customevaporated
  4. customThe residual oil was purified by flash chromatography on silica gel (100 ml.)
  5. washeluting with 50:45:5 v/v/v hexane
  6. customdichloromethane:ethyl acetate, to give a product which
  7. customwas recrystallized from a mixture of tetrahydrofuran and ether
  8. additionfrom a mixture of ethanol and water

Sources & evidence

ORD record
ord-b8333e9d2c3543d08972531cbe89450f
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

Loading…