Trifluoroacetic acid → HCID 24794622, compound

HRID 2246609Notes

Reaction equation

HRID 2246609 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][C@@H:20]([O:23][CH3:24])[CH2:19][C@H:18]2[CH2:25][NH:26][C:27](=[O:33])OC(C)(C)C)[C:13]1=[O:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:35][C:36]([F:41])([F:40])[C:37](O)=O.[CH2:42](N(CC)CC)[CH3:43].[CH3:49][N:50]([C:52]1C=[CH:56][CH:55]=[CH:54][N:53]=1)C.[C:58](OC(=O)C)(=O)C>C(Cl)Cl>[CH3:24][O:23][C@H:20]1[CH2:19][C@@H:18]([CH2:25][NH:26][C:27](=[O:33])[CH3:58])[C@@H:17]([N:14]2[CH2:15][CH2:16][C@H:12]([NH:11][C:9]3[C:55]4[C:54](=[CH:42][CH:43]=[C:37]([C:36]([F:41])([F:40])[F:35])[CH:56]=4)[N:53]=[CH:52][N:50]=3)[C:13]2=[O:34])[CH2:22][CH2:21]1.[C:27]([NH:26][CH2:25][C@@H:18]1[CH2:19][C@H:20]([O:23][CH3:24])[CH2:21][CH2:22][C@@H:17]1[N:14]1[CH2:15][CH2:16][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]1=[O:34])(=[O:33])[CH3:49]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 86618166HCID 86618166, compound

Product 2

HCID 24794622HCID 24794622, compoundHCID 86618167HCID 86618167, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A sample of tert-butyl ((1S,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-methoxycyclohexyl)methylcarbamate (0.75 g, 1.577 mmol) was dissolved in CH2Cl2 (15 mL) at room temperature. The solution was charged with trifluoroacetic acid (1.215 mL, 15.77 mmol) and stirred for 6 h. It was then evaporated and dried in vacuo. The residue was dissolved in EtOAc and washed with saturated Na2CO3, followed by brine. The organic layer was then dried over anhydrous Na2SO4, concentrated and dried in vacuo to yield a pale yellow foam. This material was dissolved in CH2Cl2 (10 mL) at room temperature. The solution was charged sequentially with triethylamine (0.659 mL, 4.73 mmol), dimethylaminopyridine (0.019 g, 0.158 mmol), and acetic anhydride (0.164 mL, 1.734 mmol). The reaction mixture was stirred for 90 min and then quenched with saturated NaHCO3. The reaction mixture was then extracted with CH2Cl2 (3×). The organic layers were combined, dried over anhydrous MgSO4, concentrated and chromatographed. The desired product, benzyl (S)-1-((1S,2S,4R)-2-(acetamidomethyl)-4-methoxycyclohexyl)-2-oxopyrrolidin-3-ylcarbamate, was obtained as a white solid. LC/MS found [M+H]+=418.4.

Workup

  1. customIt was then evaporated
  2. customdried in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated Na2CO3
  5. dry with materialThe organic layer was then dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customdried in vacuo
  8. customto yield a pale yellow foam
  9. stirringThe reaction mixture was stirred for 90 min
  10. customquenched with saturated NaHCO3
  11. extractionThe reaction mixture was then extracted with CH2Cl2 (3×)
  12. dry with materialdried over anhydrous MgSO4
  13. concentrationconcentrated
  14. customchromatographed

Sources & evidence

ORD record
ord-2cd915f3057a43c1b934dcd6c03b8272
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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