Trifluoroacetic acid → HCID 131723468, compound

HRID 2306245Notes

Reaction equation

HRID 2306245 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:21]=3)=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]1=[O:34])=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][Si:27]([C:30]([CH3:32])([CH3:31])[CH3:33])([CH3:28])[CH3:29])[CH:21]=3)=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]1=[O:34]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11092070HCID 11092070, compound

Product 1

HCID 131723468HCID 131723468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-3-(tert-Butoxycarbonylamino)-1-[3′-(tert-butyldimethylsilyloxy) biphen-2-yl]-2-oxopyrrolidine, as described above in Step E, (888 mg, 1.84 mmol) was dissolved in CH2Cl2 (20 mL), cooled to 0° C., and trifluoroacetic acid (4 mL) was added. After 3 hours, the reaction mixture was poured into saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo, to yield the above-titled compound.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1aa260fb4ded4b81ac41a608d871a381
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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