2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → (2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-(3-allyloxycarbonylmethoxyphenylcarbamoyl)pyrrolidine

HRID 260310Notes

Reaction equation

HRID 260310 reaction equation
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([C:16]([OH:18])=O)[CH2:6]1)(=[O:3])[CH3:2].[NH2:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[O:23][CH2:24][C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([C:16](=[O:18])[NH:19][C:20]2[CH:33]=[CH:32][CH:31]=[C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH:21]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 15299255(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidineHCID 22401151Allyl 3-aminophenoxyacetate

Product 1

HCID 56997989(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-(3-allyloxycarbonylmethoxyphenylcarbamoyl)pyrrolidineYield 111.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine (1.59 g, 5.82 mM), allyl 3-aminophenoxyacetate (2.5 g, 0.012M), and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (3.88 g, 0.016M) were dissolved in toluene (50 ml) and stirred 18 h at ambient temperature. The reaction mixture was diluted with ethyl acetate (150 ml) and washed with 2M hydrochloric acid (2×30 ml), water, saturated NaHCO3, and brine. Crude product was purified by chromatography on silica, using a gradient from dichloromethane to dichloromethane/diethyl ether (4:1), to give title compound (3.0 g).

Workup

  1. washwashed with 2M hydrochloric acid (2×30 ml), water, saturated NaHCO3, and brine
  2. customCrude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-2851e02060cd4180856cfb554edb335e
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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