Diisopropylethylamine → HCID 9856569, compound

HRID 1176140Notes

Reaction equation

HRID 1176140 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[NH2:10][C@H:11]([CH2:16][OH:17])[C@H:12]([CH2:14][CH3:15])[CH3:13].CCN(C(C)C)C(C)C>C(Cl)Cl>[OH:17][CH2:16][C@@H:11]([NH:10][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:8])=[O:7])[C@@H:12]([CH3:13])[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 272402724629-25-2

Product 1

HCID 9856569HCID 9856569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-thiophenesulfonyl chloride (1 g, 5.48 mmol) in CH2Cl2 (5 μL) and (S)-isoleucinol (642 mg, 5.48 mmol) was added Hunig's base (1.05 mL, 6.02 mmol). The reaction mixture was stirred at 25° C. for 24 h. The solvent was removed and the oil was dissolved in EtOAc (100 mL). The solution was washed with water (2×100 mL), brine (1×100 mL), and dried over Na2SO4. The desired sulfonamide (m/z=264.0 (M+H), rt=0.79 min) was isolated by semi-preparative RP-HPLC using the conditions outlined for example 195.

Workup

  1. customThe solvent was removed
  2. dissolutionthe oil was dissolved in EtOAc (100 mL)
  3. washThe solution was washed with water (2×100 mL), brine (1×100 mL)
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-89cc06dbc30349c28474b56b6814c808
Source dataset
uspto-grants-2010_11
Patent number
US07842718B2

Reaction notes

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