4-Toluenesulfonyl chloride → HCID 13145046, compound

HRID 2219883Notes

Reaction equation

HRID 2219883 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C@@H:13]([CH3:16])[CH2:14][OH:15]>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:15][CH2:14][C@@H:13]([NH:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH3:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 80307L-Alaninol

Product 1

HCID 13145046HCID 13145046, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

p-Toluenesulfonyl chloride (25.38 g, 133.1 mmol) was dissolved in 70 mL dry pyridine and cooled to 0° C. (S)-2-Aminopropan-1-ol (43, 5.0 g, 66 mmol) in 20 mL dry pyridine was added dropwise via an addition funnel and the resulting mixture was stirred for 20 h at RT. The reaction mixture was concentrated and the residue was partitioned between EtOAc and H2O. The organic layer was washed with 1N HCl (4×50 mL), H2O, 5% NaHCO3, brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (80% Hex:20% Acetone) to afford the title compound. MS (m/z): 384.2 (M+H) (Calc'd for C17H21NO5S2: 383.48).

Workup

  1. additionwas added dropwise via an addition funnel
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between EtOAc and H2O
  4. washThe organic layer was washed with 1N HCl (4×50 mL), H2O, 5% NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 chromatography (80% Hex:20% Acetone)

Sources & evidence

ORD record
ord-c23f55238db644c0b3a32645165aa1cd
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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