Chloroform → HCID 87976476, compound
Reaction equation
C[C:2]1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H:3]1[C:11]([OH:13])=[O:12].C(N(C(C)C)CC)(C)C.COC(OC)N1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(Cl)(Cl)[Cl:36]>>[ClH:36].[CH3:2][CH:3]([C:11]([OH:13])=[O:12])[CH2:32][CH2:31][CH2:30][CH2:29][CH3:28]Participants
Conditions
- Temperature
- 0 °C
Procedure
The dihydrochloride salt of 4-[2-(4,5,6,7-tetrahydro-1H-1,3-diazepin-S2-yl)ethyl]-piperidine (1.6 g, 5.8 mM) in methanol (12 ml) which contained MeONa (12 mM) and dimethylformamide dimethyl acetal (20 ml) was heated at 90° C. for 8 hrs. The excess of dimethylformamide dimethylacetal was removed in vacuo to give the 4-[2-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)ethyl] 1-piperidinecarboxaldehyde dimethylacetal. To the mixture of 6-aminopenicillanic acid (1.1 g, 5 mM) and diisopropylethylamine (0.96 ml) in 20 ml dry CHCl3 was added the solution (CHCl3 8 ml: MeOH 1 ml) of the above piperidine-carboxaldehyde dimetylacetal at 0° C. The reaction was stirred at 0° C. for 1 hr and then at room temperature for 3 hrs. The solvent was then removed, and water added (30 ml). The aqueous solution, washed with ethylacetate, was acidified to pH 3 with dilute aqueous HCl and purified on Sephadex LH 20 column to yield [2S-(2alpha,5alpha,6beta)]-6-[[[4-[2-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)ethyl]-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabocyclo[3.2.0]heptane-2-carboxylic acid hydrochloride (0.85 g, 38% yield)
Workup
- waitat room temperature for 3 hrs
- customThe solvent was then removed
- additionwater added (30 ml)
- washThe aqueous solution, washed with ethylacetate
- custompurified on Sephadex LH 20 column
Sources & evidence
- ORD record
- ord-5e0b7fc431ad49ceb4cfcaf912ea30af
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04537969
Reaction notes
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