2,6-Dimethylmorpholine → benzyl (RS)-alpha-[[[1-[(cis-2,6-dimethylmorpholino)carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate

HRID 275631Notes

Reaction equation

HRID 275631 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][CH:30]1[O:35][CH:34]([CH3:36])[CH2:33][NH:32][CH2:31]1>N1C=CC=CC=1>[CH3:36][C@H:34]1[CH2:33][N:32]([C:17]([C:16]([S:13]([CH2:12][CH:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])(=[O:15])=[O:14])([CH3:21])[CH3:20])=[O:18])[CH2:31][C@@H:30]([CH3:29])[O:35]1

Participants

4

Reactant 2

HCID 1108622,6-DimethylmorpholineHCID 20088482(RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

Product 1

HCID 54035129benzyl (RS)-alpha-[[[1-[(cis-2,6-dimethylmorpholino)carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In an analogous manner to that described in Example 2, paragraphs (c) and (d), by the reaction of (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride with 2,6-dimethylmorpholine in pyridine followed by chromatographic separation of the resulting diastereomers there was obtained benzyl (RS)-α-[[[1-[(cis-2,6-dimethylmorpholino)carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate, MS: 501 (M)+, as a colourless oil.

Workup

  1. customfollowed by chromatographic separation of the resulting diastereomers there

Sources & evidence

ORD record
ord-a5b82fc00fbc4409aec6f9d18730df9a
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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