Water → HCID 11779193, compound

HRID 736600Notes

Reaction equation

HRID 736600 reaction equation
[NH2:1][C@H:2]([CH3:5])[CH2:3][OH:4].C(N(C(C)C)C(C)C)C.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C(Cl)Cl>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:1][C@H:2]([CH3:5])[CH2:3][OH:4])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 80308(R)-(-)-2-Amino-1-propanolHCID 81531Diisopropylethylamine

Product 1

HCID 11779193HCID 11779193, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-Aminopropan-1-ol (2.0 g, 26.7 mmol) and N-ethyl-N,N-diisopropylamine (8.5 mL, 48.9 mmol) was added dropwise over 20 min to a cooled (0° C.) solution of 4-bromobenzenesulfonyl chloride (6.12 g, 24 mmol) in methylene chloride (20 mL). The reaction mixture was allowed to stir for 1 h. Water was added and the mixture was washed, twice, with HCl (aq, 1 M) and one time with saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulfate and evaporated to give 6.8 g, (96% yield) of the title compound: 1H NMR (CD3OD, 400 MHz) δ 7.82 (d, J=8 Hz, 2H), 7.76 (d, J=8 Hz, 2H), 3.44 (m, 1H), 3.34 (m, 3H), 1.03 (d, J=7 Hz, 3H); MS (ESI) m/z (M++1); 13C NMR (CD3OD, 100 MHz) 142.42, 133.36, 129.74, 127.90, 66.81, 52.49, 17.94

Workup

  1. washthe mixture was washed
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-5344c85c98274ad8999ff150db2b4005
Source dataset
uspto-grants-2009_09
Patent number
US07595319B2

Reaction notes

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