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Sodium Thiosulfate → 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(hydroxyamino)cyclohexylcarbamate

HRID 554749
Notes
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Reaction equation

HRID 554749 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]([NH:23]CC#N)[CH2:19][C@H:18]2[NH:27][C:28](=[O:36])[O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:13]1=[O:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:46])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+].NO.Cl>ClCCl.CO>[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]([NH:23][OH:46])[CH2:19][C@H:18]2[NH:27][C:28](=[O:36])[O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:13]1=[O:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 1317278182-(Trimethylsilyl)ethyl(1r,2s,5r)-2-((s)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(cyanomethylamino)cyclohexylcarbamate

Product 1

HCID 86618141
2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(hydroxyamino)cyclohexylcarbamate
Yield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

A stirring solution of 2-(trimethylsilyl)ethyl(1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(cyanomethylamino)cyclohexylcarbamate (400 mg, 0.76 mmol) in dichloromethane (5 mL), was cooled to 0° C. and charged with m-CPBA (372.6 mg, 2.2 eq) in portions. The mixture was stirred at room temperature for 1.5 h. Saturated Na2S2O3 solution (3 mL) and saturated NaHCO3 solution (3 mL) were added and the mixture was stirred at room temperature for 0.5 h. The mixture was diluted with dichloromethane (80 mL), washed with saturated NaHCO3 (20 mL) and brine (20 mL). The solution was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue obtained was dissolved in methanol (5 mL) and the solution was charged with NH2OH—HCl (262.7 mg, 5 eq). The mixture was stirred at 60° C. for 2.5 h. After cooling to room temperature, the mixture was diluted with dichloromethane (80 mL) and filtered through a pad of celite. The filtrate was washed with saturated NaHCO3 (2×20 mL). The aqueous washes were extracted with dichloromethane (30 mL). The dichloromethane layers were combined and washed with brine (30 mL). The solution was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(hydroxyamino)cyclohexylcarbamate (350 mg, 91%). LC/MS found [M+H]+=507.

Workup

  1. stirringthe mixture was stirred at room temperature for 0.5 h
  2. washwashed with saturated NaHCO3 (20 mL) and brine (20 mL)
  3. dry with materialThe solution was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. stirringThe mixture was stirred at 60° C. for 2.5 h
  8. temperatureAfter cooling to room temperature
  9. filtrationfiltered through a pad of celite
  10. washThe filtrate was washed with saturated NaHCO3 (2×20 mL)
  11. extractionThe aqueous washes were extracted with dichloromethane (30 mL)
  12. washwashed with brine (30 mL)
  13. dry with materialThe solution was dried over anhydrous Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbcfc3fcd1424beb8ef083809df6f6e2
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08049019B2

Reaction notes

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