Potassium Hydroxide → HCID 9908574, compound

HRID 2184691Notes

Reaction equation

HRID 2184691 reaction equation
[CH2:1]([C@H:8]([NH:16][C:17]([C:19]1[NH:23][C:22]2[S:24][C:25]([C:27]#[C:28][Si](C)(C)C)=[CH:26][C:21]=2[CH:20]=1)=[O:18])[C:9]([N:11]1[CH2:14][CH:13]([OH:15])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([C@H:8]([NH:16][C:17]([C:19]1[NH:23][C:22]2[S:24][C:25]([C:27]#[CH:28])=[CH:26][C:21]=2[CH:20]=1)=[O:18])[C:9]([N:11]1[CH2:14][CH:13]([OH:15])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 70192425HCID 70192425, compound

Product 1

HCID 9908574HCID 9908574, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using a procedure analogous to that of G. M. Whitesides et al (J. Org. Chem., 53: 2489-2496 (1988)), to a solution of 2-trimethylsilanylethynyl-6H-thieno[2,3-b]pyrrole-5-carboxylic acid [(1S)-benzyl-2-(3-hydroxy-azetidin-1-yl)-2-oxo-ethyl]-amide (110 mg, 0.02 mmol) in methanol (0.5 ml) was added a 5% aqueous solution of potassium hydroxide (7 μL, 0.06 mmol). The reaction mixture was stirred for 3 h, concentrated to remove the methanol, diluted with water, and extracted with dichloromethane. The organic phase dried over MgSO4 and concentrated to give the title product (7 mg, 77%).

Workup

  1. concentrationconcentrated
  2. customto remove the methanol
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f66ad6fbfa4646268db0142effe2db34
Source dataset
uspto-grants-2002_06
Patent number
US06399601B1

Reaction notes

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