Trifluoroacetic acid → HCID 68769573, compound

HRID 1171604Notes

Reaction equation

HRID 1171604 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C@H:18]2[C:30]([O:32][CH3:33])=[O:31])[C:13]1=[O:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]2[C:30]([O:32][CH3:33])=[O:31])[C:13]1=[O:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68768981HCID 68768981, compound

Product 1

HCID 68769573HCID 68769573, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(3R,4S)-1-tert-Butyl 3-methyl 4-((3S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-1,3-dicarboxylate (7.45 g) was dissolved in methylene chloride (20 mL) at room temperature under nitrogen, then TFA (10 mL) was added. After 3 hours, stripped the reaction 3 times from methylene chloride (25 mL). Obtained an oil which was dissolved in ethyl acetate (25 mL) and rinsed 4 times with 1.000 N NaOH (25 mL). The ethyl acetate layer was dried over sodium sulfate and stripped to give (3R,4S)-methyl 4-((3S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-3-carboxylate (4.30 g) as a white glass. Yield=73%. LCMS detects (M+H)+=376.1.

Workup

  1. customObtained an oil which
  2. washrinsed 4 times with 1.000 N NaOH (25 mL)
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate

Sources & evidence

ORD record
ord-17ad21cd35324119bf6279842478f30c
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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