Methanol → HCID 15671929, compound

HRID 1085095Notes

Reaction equation

HRID 1085095 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[O:14])=[C:8]([CH2:11][I:12])[CH2:9][S:10][C@H:5]12)=[O:2].CO.[C:29]([C:32]12[CH2:39][CH2:38][N:35]([CH2:36][CH2:37]1)[CH2:34][CH2:33]2)(=[O:31])[NH2:30]>C(OCC)(=O)C>[CH:20]([O:23][CH:39]([CH3:38])[CH3:32])([CH3:21])[CH3:19].[I-:12].[CH:1]([NH:3][C@@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[O:14])=[C:8]([CH2:11][N+:35]34[CH2:38][CH2:39][C:32]([C:29](=[O:31])[NH2:30])([CH2:37][CH2:36]3)[CH2:33][CH2:34]4)[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 101300691-Azabicyclo[2.2.2]octane-4-carboxamideHCID 14621642HCID 14621642, compound

Product 2

HCID 7914Diisopropyl EtherHCID 15671929HCID 15671929, compoundYield 196.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To an ethyl acetate solution (465 ml) of p-methoxybenzyl 7β-formamido-3-iodomethyl-3-cephem-4-carboxylate (9.3 g) there was added dropwise over 1 hour under stirring while ice-cooling a mixed solution (176 ml) of methanol and ethyl acetate (1:4 v/v) containing 4-carbamoyl quinuclidine (2.94 g). After stirring for 30 minutes, the resulting precipitate was collected by filtration, followed by washing with ethyl acetate and then diisopropyl ether to obtain the desired product (12.0 g).

Workup

  1. stirringAfter stirring for 30 minutes
  2. filtrationthe resulting precipitate was collected by filtration
  3. washby washing with ethyl acetate

Sources & evidence

ORD record
ord-87cd02c953c34862998788ad1e64f553
Source dataset
uspto-grants-1991_04
Patent number
US05008260

Reaction notes

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