4-Methylmorpholine → ethyl N-(4-[(5-nitro-1H-indol-1-yl)methyl]benzoyl)-L-phenylalaninate

HRID 2245514Notes

Reaction equation

HRID 2245514 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:47]([O:49][C:50](=[O:60])[C@H:51]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[NH2:52])[CH3:48].CN1CCOCC1>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:52][C@H:51]([C:50]([O:49][CH2:47][CH3:48])=[O:60])[CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[O:19])=[CH:16][CH:15]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 592167084-[(5-Nitro-1H-indol-1-yl)methyl]benzoic acid

Product 1

HCID 68546120ethyl N-(4-[(5-nitro-1H-indol-1-yl)methyl]benzoyl)-L-phenylalaninateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[(5-nitro-1H-indol-1-yl)methyl]benzoic acid (1.78 g, 6.0 mmol), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (1.15 g, 6.0 mmol), 1-hydroxybenzotriazole hydrate (0.81 g, 6.0 mmol), and L-phenylalanine ethyl ester hydrochloride (1.38 g, 6.0 mmol) was stirred in CH2Cl2 (150 mL). N-methylmorpholine (3.03 g, 30 mmol) was added and the mixture was stirred at room temperature for 15 h. The mixture was then washed with 0.05 N HCl and water. The resulting solution was dried with MgSO4 and concentrated to give ethyl N-{4-[(5-nitro-1H-indol-1-yl)methyl]benzoyl}-L-phenylalaninate as an off-white solid (2.55 g, 90%): MS (ESI) m/z 472; MS (ESI) m/z 470.

Workup

  1. washThe mixture was then washed with 0.05 N HCl and water
  2. dry with materialThe resulting solution was dried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-78ec117c12b743e99abf3df23a2bb43e
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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