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

HRID 1904476Notes

Reaction equation

HRID 1904476 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 (S) (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 methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methyl-indol-3-ylmethyl]-3-methoxybenzoate (T) as a foam (0.25 g, 74%); NMR: 1.62[m, 8H, (CH2)4 ], 3.68(s, 3H, NCH3), 3.83(s, 3H, COOCH3), 3.91(s, 3H, OCH3), 3.95(s, 2H, CH2Ar), 5.05(m, 1H, --CHO--), 7.11(m, 2H), 7.26(d, 1H), 7.43 (m, 2H), 7.59(br, 1H), 9.18 (br, 1H, 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-ce930f51b4a64ca18798c53aa6395995
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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