4-Toluenesulfonyl chloride → (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester

HRID 63687Notes

Reaction equation

HRID 63687 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C@@H:4]([NH2:10])[C@H:5]([OH:9])[CH:6]([CH3:8])[CH3:7].C(N(CC)CC)C.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl>[CH3:1][O:2][C:3](=[O:11])[C@@H:4]([NH:10][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=1)(=[O:28])=[O:27])[C@H:5]([OH:9])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 89995944(2R,3S)-Methyl 2-amino-3-hydroxy-4-methylpentanoate

Product 1

HCID 90000943(2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2S,3R)-2-amino-3-hydroxy-4-methyl-pentanoic acid methyl ester (0.50 g, 3.4 mmol) and triethylamine (0.69 g, 6.8 mmol) in dichloromethane (10 mL) was added 4-methyl-benzenesulfonyl chloride (0.71 g, 3.7 mmol) at 0° C. After stirring for 2 hours at room temperature, the mixture was washed with water and the organic layer was separated and then dried over sodium sulfate. After removal of solvent, the residue was used in next step without purification. MS: calc'd (MH+) 316, measured (MH+) 316.

Workup

  1. washthe mixture was washed with water
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was used in next step without purification

Sources & evidence

ORD record
ord-14ebf1bd860147438186f01ac5e90a16
Source dataset
uspto-grants-2016_09
Patent number
US09447086B2

Reaction notes

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