Dichloromethane → 3-Methylthiomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 981543Notes

Reaction equation

HRID 981543 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH2:15])[C:13](=[O:16])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11].C(Cl)Cl.[C:20]([NH:39][C:40]1[S:41][CH:42]=[C:43]([C:45](=[N:49][O:50][CH3:51])[C:46](O)=[O:47])[N:44]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(=O)C.C(N(CC)CC)C.CC(C)=O>[CH3:1][S:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:46](=[O:47])[C:45]([C:43]3[N:44]=[C:40]([NH:39][C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[S:41][CH:42]=3)=[N:49][O:50][CH3:51])[C:13](=[O:16])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11]

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 677128833-Methylthiomethyl-7-amino-ceph-3-eme-4-carboxylic acid

Product 1

HCID 1317167853-Methylthiomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 8471TriethylamineSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 2.6 g of 3-methylthiomethyl-7-amino-ceph-3-eme-4-carboxylic acid, 26 ml of methylene chloride and 3 ml of triethylamine was stirred at 20° C. under an inert atmosphere and after cooling the mixture to -20° C., an acetone suspension of the mixed anhydride of Example 3 prepared from 6 g of the triethylamine salt of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetic acid was added thereto. The mixture was stirred for 2 hours at 0° C. and was then acidified with 1 ml of acetic acid. The mixture was evaporated to dryness under reduced pressure and the residue was taken up in 50 ml of methylene chloride. The organic solution was washed with water, dried and evaporated to dryness under reduced pressure. The residue was taken up in 50 ml of ether and the mixture was vacuum filtered to obtain 8.06 g of syn isomer of 3-methylthiomethyl-7-[2-(2-tritylamino- 4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. temperatureafter cooling the mixture to -20° C.
  2. additionwas added
  3. stirringThe mixture was stirred for 2 hours at 0° C.
  4. customThe mixture was evaporated to dryness under reduced pressure
  5. washThe organic solution was washed with water
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ba7c2512239b4af6bd84377d441fc7fe
Source dataset
uspto-grants-1991_02
Patent number
US04992431

Reaction notes

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