4-Methylmorpholine → HCID 178501400, compound

HRID 1607415Notes

Reaction equation

[CH:1](=[C:8]([CH2:12][C:13](=[O:26])[NH:14][CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1.Cl.Cl.[CH3:47][O:48][C:49](=[O:58])[C@H:50]([CH2:52][C:53]1[N:57]=[CH:56][NH:55][CH:54]=1)[NH2:51].CN1CCOCC1>C(#N)C.CN(C)C=O.N1C=CC=CC=1>[CH3:47][O:48][C:49](=[O:58])[C@H:50]([CH2:52][C:53]1[N:57]=[CH:56][NH:55][CH:54]=1)[NH:51][C:9](=[O:10])[C:8](=[CH:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:12][C:13](=[O:26])[NH:14][CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 330 mg of 2-benzylidene-3-(1-naphthylmethylcarbamoyl)propionic acid, 260 mg of N,N'-disuccinimidylcarbonate and 1 ml of pyridine in 20 ml of dry acetonitrile was stirred for 3 hour at room temperature. The solution was added to a solution of 300 mg of L-histidine methyl ester dihydrochloride and 150 mg of N-methylmorpholine in 20 ml of dry N,N-dimethylformamide, and the mixture was stirred for 16 hours at 40° C. The reaction mixture was concentrated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The precipitates were collected by filtration to obtain 350 mg of N-[2-benzylidene-3-(1-naphthylmethylcarbamoyl)propionyl]-L-histidine methyl ester as a white powder.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additiona 5% aqueous sodium bicarbonate solution was added to the residue
filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record: ord-31e9289029fe4c73b7d5836dcdb84c4c
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863904

Reaction notes

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