Triethylamine → HCID 178514123, compound

HRID 1709375

Reaction equation

HRID 1709375 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH2:27][C:28]([OH:30])=[O:29])/[C:8]([NH:10][C@H:11]2[C@@H:14]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[N:13]([S:20]([OH:23])(=[O:22])=[O:21])[C:12]2=[O:24])=[O:9])[N:6]=1.C(N(CC)CC)C.C(C(CCCC)C([O-])=O)C.[Na+:48]>CO.C(OCC)(=O)C.CC(C)=O>[Na+:48].[Na+:48].[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH2:27][C:28]([OH:30])=[O:29])/[C:8]([NH:10][C@H:11]2[C@@H:14]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[N:13]([S:20]([O-:23])(=[O:21])=[O:22])[C:12]2=[O:24])=[O:9])[N:6]=1.[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH2:27][C:28]([OH:30])=[O:29])/[C:8]([NH:10][C@H:11]2[C@@H:14]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[N:13]([S:20]([O-:23])(=[O:21])=[O:22])[C:12]2=[O:24])=[O:9])[N:6]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6540466CarumonamHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 178514123HCID 178514123, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

110 g (0.235 mol) of crude (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid (obtained according to Example 41) are dispersed in 4.7 l of methanol and treated with 72.3 ml (0.518 mol) of triethylamine and 282.9 ml (0.566 mol) of a 2N solution of sodium 2-ethylcaproate in ethyl acetate. The solution obtained is stirred for 10 minutes, diluted with 9 l of acetone and concentrated to 3 l. The residual suspension is diluted with 3 l of acetone, filtered and the crystalline salt is washed with ether and dried. 108.59 g (90.5%) of (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(carboxymethoxy)-imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid disodium salt are obtained. This crude salt is dissolved in 420 ml of water. 1050 ml of ethanol are added thereto and subsequently (after a few minutes) a further 210 ml of ethanol are added. The solution is turbid and is stirred for 1 hour. 1770 ml of ethanol are now added dropwise thereto within 2 hours. After stirring for a further 1 hour and cooling to 0° C., the precipitate is filtered off and washed with ethanol. The crystals obtained are dispersed in 170 ml of ethanol and 680 ml of ether, filtered off and washed with ether. After drying under greatly reduced pressure at 40° C., there obtained 102.9 g (85.5%) of (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid disodium salt.

Workup

  1. customThe solution obtained
  2. concentrationconcentrated to 3 l
  3. additionThe residual suspension is diluted with 3 l of acetone
  4. filtrationfiltered
  5. washthe crystalline salt is washed with ether
  6. customdried

Sources & evidence

ORD record
ord-8ed6fac4d3a048cfa3a08018758bba27
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Linked notes

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