Water → HCID 7270101, compound

HRID 736602Notes

Reaction equation

HRID 736602 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH2:6])[CH3:5].C(N(C(C)C)C(C)C)C.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>C(Cl)Cl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 70215362-Propanamine, 1-methoxy-, (2S)-

Product 1

HCID 7270101HCID 7270101, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S)-2-Methoxy-1-methylethylamine (7.34 g, 82.4 mmol) and N-ethyl-N,N-diisopropylamine (19.1, 110 mmol) was added dropwise over 20 min to a cooled (0° C.) solution of 4-bromobenzenesulfonyl chloride (14.0 g, 55 mmol) in methylene chloride (200 mL). The reaction mixture was allowed to stir for 1 h. Water was added and the mixture was washed, twice, with HCl (1 M) and once with saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulfate and evaporated to give 15.1 g, (94% yield) of the title compound: 1H NMR (CDCl3, 400 MHz) δ 7.76 (d, J=8 Hz, 2H), 7.65 (d, J=8 Hz, 2H), 4.97 (m, 1H), 3.46 (m, 1H), 3.23 (m, 5H), 1.12 (d, J=7 Hz, 3H); MS (ESI) m/z 308 and 310 (M++1)

Workup

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

Sources & evidence

ORD record
ord-8e601d4a56e545d39431cd9bd3a7b66a
Source dataset
uspto-grants-2009_09
Patent number
US07595319B2

Reaction notes

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