4-Toluenesulfonyl chloride → (S)-2-(Methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate

HRID 660020Notes

Reaction equation

HRID 660020 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH:12][C@@H:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([NH:16][CH3:17])=[O:15].CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[CH3:8][C:7]1[CH:9]=[CH:10][C:4]([S:1]([O:12][C@@H:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([NH:16][CH3:17])=[O:15])(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 12281461(S)-2-Hydroxy-N-methyl-2-phenylacetamide

Product 1

HCID 57354974(S)-2-(Methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonateYield 61.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TsCl (4.75 g, 25 mmol, 1.0 eq) was added portion-wise at rt to a solution of 37 (4.13 g, 25 mmol, 1.0 eq) and DIPEA (3.22 g, 4.4 mL, 25 mmol, 1.0 eq) in dichloromethane (100 mL). The reaction mixture was stirred at rt for 5 h, then was concentrated under reduced pressure to give an oil. The crude oil was dissolved in ethyl acetate (150 mL), and the solution was washed sequentially with water (100 mL), saturated sodium bicarbonate solution (2×75 mL) and brine (75 mL). The organic solution was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to near dryness. The solid was triturated with methyl t-butyl ether (100 mL), filtered and dried to give 4.89 g (61%) of 38 as a white solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto give an oil
  3. washthe solution was washed sequentially with water (100 mL), saturated sodium bicarbonate solution (2×75 mL) and brine (75 mL)
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe solid was triturated with methyl t-butyl ether (100 mL)
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-f9df6a27ffec47fbb7f6a5f6fe5a1f36
Source dataset
uspto-grants-2011_12
Patent number
US08084464B2

Reaction notes

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