Pyridine → (R)-tert-butyl 2-fluoro-2 oxo-1-(thiophen-3-yl)ethylcarbamate

HRID 1690231Notes

Reaction equation

HRID 1690231 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:26]>C(Cl)Cl>[F:26][C:10](=[O:11])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]1[CH:17]=[CH:16][S:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 7023006(R)-2-((tert-Butoxycarbonyl)amino)-2-(thiophen-3-yl)acetic acid

Product 1

HCID 57788121(R)-tert-butyl 2-fluoro-2 oxo-1-(thiophen-3-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To (R)-2-(tert-butoxycarbonylamino)-2-(thiophen-3-yl)acetic acid in CH2Cl2 cooled to −10° C. was added pyridine and cyanuric fluoride. The solution was stirred for 1 hour at −10° C., quenched with ice and extracted with CH2Cl2 and ice cold water, dried (Na2SO4), filtered and evaporated to give (R)-tert-butyl 2-fluoro-2 oxo-1-(thiophen-3-yl)ethylcarbamate.

Workup

  1. customquenched with ice
  2. extractionextracted with CH2Cl2 and ice cold water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f9bdb0b1240d4803b0677c6b0609647e
Source dataset
uspto-grants-2012_04
Patent number
US08153654B2

Reaction notes

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