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Propylene Oxide → (3S,4S)-4-azido-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine

HRID 978839
Notes
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Reaction equation

HRID 978839 reaction equation
O=C(Cl)OC(Cl)(Cl)Cl.[Cl:9][CH2:10][C:11]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19](=[N:23][O:24][CH3:25])[C:20]([OH:22])=O)[N:18]=1)=[O:12].[NH2:26][C@H:27]1[C@H:30]([N:31]=[N+:32]=[N-:33])[NH:29][C:28]1=[O:34].C1OC1C>C(Cl)Cl.C(N(CC)CC)C.CN(C=O)C>[N:31]([C@@H:30]1[NH:29][C:28](=[O:34])[C@H:27]1[NH:26][C:20](=[O:22])[C:19]([C:17]1[N:18]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][Cl:9])[S:15][CH:16]=1)=[N:23][O:24][CH3:25])=[N+:32]=[N-:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6378Propylene OxideHCID 10426DiphosgeneHCID 581157C8H8ClN3O4SHCID 54269820(3S,4S)-3-amino-4-azido-2-oxoazetidine

Product 1

HCID 53886787(3S,4S)-4-azido-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent2×
HCID 8471TriethylamineSolvent2×

Procedure

To a solution of 0.127 g of DMF in 5 ml of methylene chloride is added 0.104 ml of diphosgene at -10° C. The mixture is stirred for 30 minutes at room temperature, followed by addition of a solution of 15 ml of methylene chloride containing 0.483 g of 2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetic acid and 0.176 g of triethylamine at -70° C. The mixture is stirred for two hours at -25° C., then cooled to -70° C., followed by addition of 0.352 g of triethylamine, 0.40 g of tosyl salt of (3S,4S)-3-amino-4-azido-2-oxoazetidine and 2 ml of propylene oxide. The temperature of the mixture is raised up to room temperature in the course of one hour while stirring, followed by ice-cooling for one hour. The crystals separated out are collected by filtration to yield 0.383 g of (3S,4S)-4-azido-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine.

Workup

  1. stirringThe mixture is stirred for two hours at -25° C.
  2. temperaturecooled to -70° C.
  3. temperatureThe temperature of the mixture is raised up to room temperature in the course of one hour
  4. stirringwhile stirring
  5. temperaturecooling for one hour
  6. customThe crystals separated out
  7. filtrationare collected by filtration

Sources & evidence

ORD record
ord-3912d9cf2b1e4ba1b89b9e4bb4734c22
Source dataset
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04665067

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes