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Phosphate → (5R, 6E)-6-[(10-benzyl-11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepin-8-yl)methylene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

HRID 1744939
Notes
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Reaction equation

HRID 1744939 reaction equation
P([O-])([O-])([O-])=O.[N+](C1C=CC(C[O:14][C:15]([C:17]2[N:18]3[CH:21]([S:22][CH:23]=2)[C:20]([CH:25](OC(=O)C)[C:26]2[CH:48]=[CH:47][C:29]4[O:30][C:31]5[CH:46]=[CH:45][CH:44]=[CH:43][C:32]=5[C:33](=[O:42])[N:34]([CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:28]=4[CH:27]=2)(Br)[C:19]3=[O:53])=[O:16])=CC=1)([O-])=O>C1COCC1.[Pd]>[CH2:35]([N:34]1[C:33](=[O:42])[C:32]2[CH:43]=[CH:44][CH:45]=[CH:46][C:31]=2[O:30][C:29]2[CH:47]=[CH:48][C:26](/[CH:25]=[C:20]3/[C@@H:21]4[N:18]([C:19]/3=[O:53])[C:17]([C:15]([OH:16])=[O:14])=[CH:23][S:22]4)=[CH:27][C:28]1=2)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 1061PhosphateHCID 684449316-[Acetoxy-(10-benzyl-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepin-8-yl)-methyl]-6-bromo-7oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Product 1

HCID 10457946(5R, 6E)-6-[(10-benzyl-11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepin-8-yl)methylene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic AcidYield 24%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

A 0.5M phosphate buffer solution (pH 6.5) was added to a solution of 6-[acetoxy-(10-benzyl-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepin-8-yl)-methyl]-6-bromo-7oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (0.210 g, 0.273 mmole) in THF, followed by 10% Pd—C (0.0546 g). The reaction mixture then was hydrogenated at 40 psi for three hours. Filtered through a celite pad and removed the THF by rotary evaporation, extracted the mixture with ethyl acetate and washed with water and brine. Dried the organic layer with sodium sulfate and filtered and concentrated. Dissolved the NaHCO3 with minimal amount of distal water and added it to the reaction mixture along with a small amount of ethyl acetate until the pH value reaches 7–8, evaporated the ethyl acetate. Purified with reverse phase column (MCI Gel CHP20P) with varying amounts of acetonitrile (0%-20%) in water. Removed the acetonitrile and water by rotary evaporation, and freeze-dried the compound. Obtained the desired material (yellow solid) in 24% yield.Mp: 179° C. 1H NMR (DMSO) δ 1.755–1.825 (s, 1H), 2.497–2.506 (d, 2H), 5.243–5.434 (m, 2H), 6.516–6.770 (m, 1H), 7.039–7.792 (m, 11H).

Workup

  1. filtrationFiltered through a celite pad
  2. customremoved the THF
  3. customby rotary evaporation
  4. extractionextracted the mixture with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialDried the organic layer with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionDissolved the NaHCO3 with minimal amount of distal water
  10. additionadded it to the reaction mixture along with a small amount of ethyl acetate until the pH value
  11. customevaporated the ethyl acetate
  12. customPurified with reverse phase column (MCI Gel CHP20P) with varying amounts of acetonitrile (0%-20%) in water
  13. customRemoved the acetonitrile and water
  14. customby rotary evaporation
  15. customfreeze-dried the compound

Sources & evidence

ORD record
ord-9c0b7bbb1d4d42d5970fee150cc265cc
Source dataset
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07018997B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes