2-Chloro-1-methylpyridinium iodide → HCID 88629683, compound

HRID 1195053Notes

Reaction equation

HRID 1195053 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[NH2:10][C:11]1[S:12][CH:13]=[C:14](/[C:16](=[N:20]/[O:21][CH2:22][CH2:23][I:24])/[C:17]([OH:19])=O)[N:15]=1.[NH2:25][C@H:26]1[C@@H:29]([CH2:30][O:31][C:32](=[O:34])[NH2:33])[N:28]([S:35]([OH:38])(=[O:37])=[O:36])[C:27]1=[O:39]>C(N(CC)CC)C>[NH2:10][C:11]1[S:12][CH:13]=[C:14](/[C:16](=[N:20]/[O:21][CH2:22][CH2:23][I:24])/[C:17]([NH:25][C@H:26]2[C@@H:29]([CH2:30][O:31][C:32](=[O:34])[NH2:33])[N:28]([S:35]([OH:38])(=[O:36])=[O:37])[C:27]2=[O:39])=[O:19])[N:15]=1

Participants

5

Reactant 3

HCID 1670692-Chloro-1-methylpyridinium iodideHCID 13473381HCID 13473381, compoundHCID 21269060HCID 21269060, compound

Product 1

HCID 88629683HCID 88629683, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

7.7 g of 2-chloro-1-methyl-pyridinium iodide are added to a solution of 6.8 g of 2-(2-amino-4-thiazolyl)-2-[(Z)-(2-iodoethoxy)imino]-acetic acid, 4.8 g of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid and 8.4 g of triethylamine in 50 ml of dimethylformide and the mixture is stirred for 2 hours. After removal of the solvent under reduced pressure at about 25° C., the residue is taken up in 250 ml of water and washed with 100 ml of ethyl acetate and twice with 100 ml of dichloromethane. After the addition of 20.3 g of tetra-n-butylammonium hydrogen sulphate, the mixture is adjusted to pH 6-7 using 70 ml of saturated sodium bicarbonate solution and extracted four times with 100 ml of dichloromethane each time. The combined extracts are washed with 50 ml of water. The product is then precipitated by the addition of 7.5 ml of formic acid. After washing with acetone and ether, there are obtained 5.6 g of (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(2-iodoethoxy)imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid.

Workup

  1. customAfter removal of the solvent under reduced pressure at about 25° C.
  2. washwashed with 100 ml of ethyl acetate and twice with 100 ml of dichloromethane
  3. additionAfter the addition of 20.3 g of tetra-n-butylammonium hydrogen sulphate
  4. extractionextracted four times with 100 ml of dichloromethane each time
  5. washThe combined extracts are washed with 50 ml of water
  6. customThe product is then precipitated by the addition of 7.5 ml of formic acid
  7. washAfter washing with acetone and ether, there

Sources & evidence

ORD record
ord-32f98a64562648bf874b630e93f551c5
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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