Water → HCID 68980698, compound

HRID 1516290Notes

Reaction equation

HRID 1516290 reaction equation
C(OC([NH:8][C@@H:9]([CH3:32])[C:10]([O:12][CH2:13][C@@H:14]1[C:18]([OH:20])([CH3:19])[C@:17]([F:22])([CH3:21])[CH:16]([N:23]2[CH:28]=[C:27]([CH3:29])[C:26](=[O:30])[NH:25][C:24]2=[O:31])[O:15]1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O.O.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:8][CH:9]([CH3:32])[C:10]([O:12][CH2:13][C@@H:14]1[C:18]([OH:20])([CH3:19])[C@:17]([F:22])([CH3:21])[CH:16]([N:23]2[CH:28]=[C:27]([CH3:29])[C:26](=[O:30])[NH:25][C:24]2=[O:31])[O:15]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57867361HCID 57867361, compound

Product 1

HCID 68980698HCID 68980698, compoundYield 556.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2S)-((2R,4R)-4-fluoro-3-hydroxy-3,4-dimethyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 2-(tert-butoxycarbonylamino)propanoate (Example 47, about 0.005 g, 0.01 mmol) in dichloromethane was added trifluoroacetic acid (about 0.01 ml, 0.10 mmol) at about 0° C. and stirred at room temperature for about 1 hour. Completion of the reaction monitored by thin-layer chromatography and water added to the reaction mixture. The aqueous layer was added to saturated sodium bicarbonate and extracted with ethyl acetate, the combined organic layers were washed with brine and dried over sodium sulphate, Concentrated under reduced pressure to afford (0.02 g) crude compound. ES Mass: [M+1] 360 (100%).

Workup

  1. additionadded to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationConcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa616dc1c2fd4097baead71f2cd957a5
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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