Dimethylformamide → HCID 54150686, compound

HRID 2231518Notes

Reaction equation

HRID 2231518 reaction equation
C[N:2]([CH:4]=[O:5])C.[O:6]=[C:7](Cl)[O:8][C:9](Cl)(Cl)Cl.[Cl:14][CH2:15][C:16]([NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24](=[N:28][O:29][CH:30]([CH3:32])[CH3:31])[C:25]([OH:27])=O)[N:23]=1)=[O:17].[CH2:33]([N:35](CC)CC)C.[CH2:40](Cl)Cl>C1COCC1>[C:7]([O:8][C@@H:9]1[NH:2][C:4](=[O:5])[C@H:33]1[NH:35][C:25](=[O:27])[C:24]([C:22]1[N:23]=[C:19]([NH:18][C:16](=[O:17])[CH2:15][Cl:14])[S:20][CH:21]=1)=[N:28][O:29][CH:30]([CH3:32])[CH3:31])(=[O:6])[CH3:40]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6344Dichloromethane2×HCID 8471Triethylamine2×HCID 10426DiphosgeneHCID 54354958HCID 54354958, compound

Product 1

HCID 54150686HCID 54150686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

On the other hand, to a solution of 0.410 g of DMF in 10 ml of methylene chloride is added 0.475 g of diphosgene at -10° C. and the mixture is stirred at room temperature for 15 minutes. A solution of 1.23 g of 2-(2-chloroacetamidothiazol-4-yl)-2-isopropoxyiminoacetic acid (syn-isomer) and 0.530 g of triethylamine in 15 ml of methylene chloride is added dropwise at -60° to -50° C. and the mixture is stirred at -40~-30° C. for 1.5 hours. Then, 0.490 g of triethylamine is added at -60°~-50° C. and the above prepared THF solution is further added. The mixture is allowed to stand at room temperature over 1 hour and the solvent is distilled off under reduced pressure. The residual ethyl acetate solution is washed with water and concentrated under reduced pressure. Purifying the residue on a silica gel column (ethyl acetate:n-hexane=2:1) yields 1.23 g of (3S,4S)-4-acetoxy-3-[2-(2-chloroacetamidothiazol-4-yl)-2-isopropoxyiminoacetamido]-2-oxoazetidine (syn-isomer).

Workup

  1. stirringthe mixture is stirred at -40~-30° C. for 1.5 hours
  2. additionis further added
  3. waitto stand at room temperature over 1 hour
  4. distillationthe solvent is distilled off under reduced pressure
  5. washThe residual ethyl acetate solution is washed with water
  6. concentrationconcentrated under reduced pressure
  7. customPurifying the residue on a silica gel column (ethyl acetate:n-hexane=2:1)

Sources & evidence

ORD record
ord-f1e8385ed53f4aa9a7dbdeeabe95e3b3
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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