Methanol → HCID 131710482, compound

HRID 1287605Notes

Reaction equation

HRID 1287605 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([NH:7][CH:8]1[C:20](=[O:21])[N:10]2[C:11]([C:17]([OH:19])=[O:18])=[C:12]([O:15][CH3:16])[CH2:13][S:14][C@H:9]12)=[S:6])#[N:2].CO.C(OCC)(=O)CCCCC.[K].[K+:35].[Br-]>CCOCC>[K+:35].[C:1]([CH2:3][CH2:4][C:5]([NH:7][CH:8]1[C:20](=[O:21])[N:10]2[C:11]([C:17]([O-:19])=[O:18])=[C:12]([O:15][CH3:16])[CH2:13][S:14][C@H:9]12)=[S:6])#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 253877Potassium BromideHCID 53628223HCID 53628223, compoundHCID 131710483HCID 131710483, compound

Product 1

HCID 131710482HCID 131710482, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7-Cyanomethylthioacetamido-3-methoxy-3-cephem-4-carboxylic acid (35 mg.) is dissolved in 1 ml. of methanol and 50 μ l of 2.5 M potassium 2-ethyl hexanoate is added. Addition of ether causes precipitation of a very hygroscopic solid. All solvent is removed in vacuo from the mixture and the residue is solidified by the addition of acetonitrile. The desired potassium salt is collected by filtration and dried yielding 19 mg; NMR (DMSO d6 δ) 3.43 (m, CH2),3.52 (s, NCCH2SCH2CO--) 3.76 (s,OCH3), 4.10 (d, J=4Hz, H6), 5.30 (q, J=4, 9.5 Hz, H7), 9.03 (d, J=9.5 Hz,NH); νmax (KBr) 3575, 3270, 2240, 1750, 1630, 1595, 1540 cm-1.

Workup

  1. customprecipitation of a very hygroscopic solid
  2. customAll solvent is removed in vacuo from the mixture
  3. additionthe residue is solidified by the addition of acetonitrile
  4. filtrationThe desired potassium salt is collected by filtration
  5. customdried
  6. customyielding 19 mg

Sources & evidence

ORD record
ord-6b87ab3dfa1943b58161ec8bad1aab40
Source dataset
uspto-grants-1976_10
Patent number
US03985746

Reaction notes

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