Hydrochloric Acid → Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

HRID 1646340Notes

Reaction equation

HRID 1646340 reaction equation
Cl[C:2]([O:4][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:3].[NH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[CH:15]=[C:14]2[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33].CN1CCOCC1.Cl>ClCCl>[CH:5]1([O:4][C:2]([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[CH:15]=[C:14]3[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[O:3])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 2735892Cyclopentyl chloroformateHCID 11209537Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

Product 1

HCID 11453373Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoateYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopentyl chloroformate (0.11 g.) was added to a stirred solution of methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (D) (0.25 g.) and N-methylmorpholine (0.23 g.) in dichloromethane (3 ml.), under an atmosphere of nitrogen. The mixture was stirred for 2 hours and then poured into 1M hydrochloric acid (20 ml.). This acid mixture was extracted with ethyl acetate (2×30 ml.). The combined extracts were washed with saturated brine (20 ml.), dried (MgSO4), and evaporated to give a viscous oil. This was purified by flash chromatography on silica gel (50 ml.), eluting with 3:7 v/v ethyl acetate:hexane, to give the title compound as a foam (0.25 g., 74%): NMR: 1.62 [m,8 H, (CH2)4 ], 3.68 (s,3 H, NCH3), 3.83 (s,3 H, CO.OCH3), 3.91 (s,3 H, OCH3), 3.95 (s, 2 H, CH2.Ar), 5.05 (m,1 H, --CHO--), 7.11 (m,2 H), 7.26 (d, 1 H), 7.43 (m,2 H), 7.59 (br,1 H), 9.18 (br,1 H, NH).

Workup

  1. extractionThis acid mixture was extracted with ethyl acetate (2×30 ml.)
  2. washThe combined extracts were washed with saturated brine (20 ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a viscous oil
  6. customThis was purified by flash chromatography on silica gel (50 ml.)
  7. washeluting with 3:7 v/v ethyl acetate

Sources & evidence

ORD record
ord-56dfcd5b7b0241719541a4737c87f7fc
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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