HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-(N-benzyloxycarbonyl-L-threonyl)-O-methoxymethyl-N-methyl-beta-benzoyloxytyrosine methyl ester

HRID 1648179
Notes
Print preview

Reaction equation

HRID 1648179 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[C@@H:13]([CH3:15])[OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21](=[O:45])[C@H:22]([CH:25]([O:36][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=1)[NH:23][CH3:24].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>ClCCl>[CH3:19][O:20][C:21](=[O:45])[C@H:22]([CH:25]([O:36][C:37](=[O:44])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=1)[N:23]([C:16](=[O:18])[C@H:12]([C@@H:13]([CH3:15])[OH:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 88217N-((Benzyloxy)carbonyl)-L-threonineHCID 53867281O-methoxymethyl-N-methyl-beta-benzoyloxytyrosine methyl ester

Product 1

HCID 54308932N-(N-benzyloxycarbonyl-L-threonyl)-O-methoxymethyl-N-methyl-beta-benzoyloxytyrosine methyl esterYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of N-benzyloxycarbonyl-L-threonine (3.7 g) and O-methoxymethyl-N-methyl-β-benzoyloxytyrosine methyl ester (threo isomer) (3.11 g) in dichloromethane (50 ml) was added ethyl 1,2-dihydro-2-ethoxy-1-quinolinecarboxylate (2.9 g). After stirring for 20 hours at room temperature, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (50 ml) and washed with dil. hydrochloric acid, sodium bicarbonate aqueous solution and water. After evaporation, the residue was put on a column of silica gel (MERCK 7734, 100 g) and eluted with n-hexane-ethyl acetate (1:1, V/V) to give N-(N-benzyloxycarbonyl-L-threonyl)-O-methoxymethyl-N-methyl-β-benzoyloxytyrosine methyl ester (threo isomer) (2.04 g).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with dil. hydrochloric acid, sodium bicarbonate aqueous solution and water
  4. customAfter evaporation
  5. washeluted with n-hexane-ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-0433a03628504e1c860a46a55accd801
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05436140

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes