Water → HCID 23537236, compound

HRID 1792472Notes

Reaction equation

HRID 1792472 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH:14][C@H:15]([C:21]1[S:22][C:23]2[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:24]=2[N:25]=1)[CH2:16][CH2:17][C:18]([NH2:20])=O.N1C=CC=CC=1.O>O1CCCC1>[OH:14][C@H:15]([C:21]1[S:22][C:23]2[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:24]=2[N:25]=1)[CH2:16][CH2:17][C:18]#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 23537235HCID 23537235, compound

Product 1

HCID 23537236HCID 23537236, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.33 mL trifluoroacetic anhydride was added to a solution of 556 mg of (4S)-4-hydroxy-4-(6-iodo-1,3-benzothiazol-2-yl)butane amide obtained in Production Example 299 and 0.25 mL pyridine in tetrahydrofuran under ice-cooling, and the mixture was stirred for 2 hours. Water was added thereto, the reaction solution was then extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate and purified by NH silica gel chromatography. The product was recrystallized from ethanol/ethyl acetate/hexane, to give 390 mg of the title compound as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionthe reaction solution was then extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. custompurified by NH silica gel chromatography
  5. customThe product was recrystallized from ethanol/ethyl acetate/hexane

Sources & evidence

ORD record
ord-d4ee081e2c314b2999239ecf24ab5827
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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