Hydrochloric Acid → HCID 67688232, compound

HRID 373349Notes

Reaction equation

HRID 373349 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[H][H].[C:15]1([CH2:21][C:22]([NH:24][CH:25]2[C:56](=[O:57])[N:27]3[C:28]([C:40]([O:42][CH:43]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[C:29](OS(C(F)(F)F)(=O)=O)[CH2:30][S:31][C@H:26]23)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>ClCCl>[C:15]1([CH2:21][C:22]([NH:24][CH:25]2[C:56](=[O:57])[N:27]3[C:28]([C:40]([O:42][CH:43]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)=[O:41])=[C:29]([S:1][C:2]4[S:3][C:4]5[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=5[N:6]=4)[CH2:30][S:31][C@H:26]23)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 14167862HCID 14167862, compoundHCID 178418361HCID 178418361, compoundHCID 178418395HCID 178418395, compound

Product 1

HCID 67688232HCID 67688232, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

2-Mercaptobenzothiazole (0.59 g, 0.00353 mole) was dissolved in dry dichloromethane (5 mL), and the resulting mixture was treated at 0° C. with sodium hydride (0.141 g of a 1:1 mineral oil dispersion, 0.00294 mole). Evolution of hydrogen was complete in 15 min, and, after cooling to -30° C., the mixture was treated with a solution of diphenylmethyl 7- phenylacetamido-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate (IVa, 1.858 g, 0.00294 mole) in dichloromethane (25 mL) over a 1-2 min period. The mixture was stirred 16 h at -15° C. and then 4 h at 0° C. in order to consume all of compound IVa (the reaction was monitered by HPLC). (Reaction at higher temperature induces formation of the Δ2 -isomer of compound IIc.) Dilute hydrochloric acid (0.5N, 10 mL) was added to the reaction mixture, followed by extracting the mixture with dichloromethane and drying (sodium sulfate) to yield the title product as a crude product which was recrystallized from dichloromethane/ether at 0° C. overnight.

Workup

  1. custom4 h at 0° C. in order to consume all of compound IVa (the reaction
  2. custom(Reaction at higher temperature
  3. extractionby extracting the mixture with dichloromethane
  4. dry with materialdrying (sodium sulfate)

Sources & evidence

ORD record
ord-5cca0ebf06e741819193a0e5eb46fc5b
Source dataset
uspto-grants-1992_11
Patent number
US05162521

Reaction notes

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