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

HRID 1587287Notes

Reaction equation

HRID 1587287 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]

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 6344DichloromethaneSolvent

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-74af542971c849c0b9d77a298c4151ab
Source dataset
uspto-grants-1993_06
Patent number
US05217952

Reaction notes

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