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Triethylamine → 1-Tert-butoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane

HRID 1457973
Notes
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Reaction equation

HRID 1457973 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH:16]2[C:13]([C:18]([OH:20])=[O:19])([CH2:14][CH2:15]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](N(CC)CC)C.C1(P(N=[N+]=[N-])([C:36]2[CH:41]=[CH:40]C=CC=2)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C)(C)C>[C:41]([O:19][C:18]([C:13]12[CH2:14][CH2:15][CH:16]1[CH2:17][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:12]2)=[O:20])([CH3:40])([CH3:36])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 22100508HCID 22100508, compound

Product 1

HCID 221005281-Tert-butoxycarbonyl-3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane

Reagents, catalysts & solvents 1

HCID 6386
tert-Butanol
Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-benzyloxycarbonyl-3-azabicyclo[3.2.0]heptane-1-carboxylic acid (2.60 mmol) in tertiary butanol (15 ml) were added 0.474 ml (3.4 mmol) of triethylamine and 0.733 ml (3.4 mmol) of diphenylphosphorylazide, followed by 9 hours of stirring at 70° C. After cooling to room temperature, the reaction solution was poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 642.2 mg (1.78 mmol, 68.4% for 2 steps from Reference Example B-7) of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent
  6. customthe resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8c5277df889a4d6ab77eeb538eafe52d
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05849757

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes