Triethylamine → (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester

HRID 63688Notes

Reaction equation

HRID 63688 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C@H:5]([OH:9])[CH:6]([CH3:8])[CH3:7].[O-]S(C(F)(F)F)(=O)=O.[C:30]1(C(C2C=CC=CC=2)=C[SH2+])C=CC=C[CH:31]=1.C(N(CC)CC)C>ClCCl.O>[CH3:1][O:2][C:3]([C@@H:4]1[C@@H:5]([CH:6]([CH3:8])[CH3:7])[O:9][CH2:31][CH2:30][N:10]1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90000943(2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl esterHCID 91658733HCID 91658733, compound

Product 1

HCID 89995945(2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester (0.4 g, 1.27 mmol) and diphenylvinylsulfonium triflate (0.5 g, 1.4 mmol) in dichloromethane (10 mL) was added triethylamine dropwise at 0° C. After stirring for 12 hours, the mixture was diluted with water, and then extracted with ethyl acetate, then dried over sodium sulfate. After removal of solvent, the residue was purified by flash chromatopraphy (eluented with ethyl acetate/hexane=1:4) to afford the product as a white solid. MS: calc'd (MH+) 342, measured (MH+) 342.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customAfter removal of solvent
  4. customthe residue was purified by flash chromatopraphy (eluented with ethyl acetate/hexane=1:4)

Sources & evidence

ORD record
ord-9c044b0d60d347c288a633b47d8a2491
Source dataset
uspto-grants-2016_09
Patent number
US09447086B2

Reaction notes

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