Triethylamine → HCID 10382351, compound

HRID 2242332Notes

Reaction equation

HRID 2242332 reaction equation
[NH2:1][C@H:2]([CH2:7][OH:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].C(N(CC)CC)C.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24]>C1COCC1>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:1][C@H:2]([CH2:7][OH:8])[C@@H:3]([CH3:4])[CH2:5][CH3:6])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5204032-Bromobenzenesulfonyl chlorideHCID 272402724629-25-2

Product 1

HCID 10382351HCID 10382351, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S) isoleucinol (23 mg, 0.2 mmol) in THF (3 mL) was added triethylamine (46 μL, 0.24 mmol) and 2-bromobenzenesulfonyl chloride (51 mg, 0.2 mmol). The solution was stirred for 8 to 16 hours, then concentrated. The residue was dissolved in MeOH (1.5 mL) and purified by semi-preparative RP-HPLC using the following conditions:

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH (1.5 mL)
  3. custompurified by semi-preparative RP-HPLC

Sources & evidence

ORD record
ord-1752b15242ce42c985feadc27fc1d03b
Source dataset
uspto-grants-2010_03
Patent number
US07671075B2

Reaction notes

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