4-Methylmorpholine → 3-Acetoxymethyl-7beta-[2-(2-tritylamino-4-thiazolyl)-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 1395695Notes

Reaction equation

HRID 1395695 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([CH2:26][C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[CH3:45][C:46]([O:48][CH2:49][C:50]1[CH2:59][S:58][C@@H:53]2[C@H:54]([NH2:57])[C:55](=[O:56])[N:52]2[C:51]=1[C:60]([OH:62])=[O:61])=[O:47]>O1CCCC1.O>[C:46]([O:48][CH2:49][C:50]1[CH2:59][S:58][C@@H:53]2[C@H:54]([NH:57][C:27](=[O:28])[CH2:26][C:24]3[N:25]=[C:21]([NH:20][C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[S:22][CH:23]=3)[C:55](=[O:56])[N:52]2[C:51]=1[C:60]([OH:62])=[O:61])(=[O:47])[CH3:45]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 4413287-Aminocephalosporanic acidHCID 13631022{2-[(Triphenylmethyl)amino]-1,3-thiazol-4-yl}acetic acid

Product 1

HCID 1317117723-Acetoxymethyl-7beta-[2-(2-tritylamino-4-thiazolyl)-acetamido]-ceph-3-eme-4-carboxylic acidYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-20 °C

Procedure

A mixture of 801 mg of 2-tritylamino-4-thiazolylacetic acid, 10 ml of dry tetrahydrofuran and 2 ml of a molar solution of N-methyl-morpholine in tetrahydrofuran was stirred at -20° C. and 2 ml of a molar solution of isobutyl chloroformate in tetrahydrofuran were slowly added thereto. The mixture was stirred and a solution of 544 mg of 7-amino-cephalosporanic acid in 10 ml of water and 2.4 ml of a molar solution of N-methyl-morpholine in tetrahydrofuran was added thereto. The mixture was stirred with reheating and the solvent was evaporated. The residue was diluted with water and 2 ml of 2 N hydrochloric acid were added. The mixture was vacuum filtered and the product was dried to obtain 1.16 g of 3-acetoxymethyl-7β-[2-(2-tritylamino-4-thiazolyl)-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. stirringThe mixture was stirred
  2. stirringThe mixture was stirred
  3. customthe solvent was evaporated
  4. additionThe residue was diluted with water and 2 ml of 2 N hydrochloric acid
  5. additionwere added
  6. filtrationfiltered
  7. customthe product was dried

Sources & evidence

ORD record
ord-bd82c27db86940e88240b47c707a2b45
Source dataset
uspto-grants-1980_05
Patent number
US04205072

Reaction notes

Loading…