Phosphoric Acid → HCID 88784322, compound

HRID 1732694Notes

Reaction equation

HRID 1732694 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].ClN1C(=O)CCC1=O.[Cl:19][CH2:20][C:21](=[O:46])[CH2:22][C:23]([NH:25][CH:26]1[C:44](=[O:45])[N:28]2[C:29]([C:41]([OH:43])=[O:42])=[C:30]([CH2:33][S:34][C:35]3[S:39][C:38]([CH3:40])=[N:37][N:36]=3)[CH2:31][S:32][C@H:27]12)=[O:24].P(=O)(O)(O)O.[Cl-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[Cl:19][CH2:20][C:21](=[O:46])[CH:22]([S:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])[C:23]([NH:25][CH:26]1[C:44](=[O:45])[N:28]2[C:29]([C:41]([OH:43])=[O:42])=[C:30]([CH2:33][S:34][C:35]3[S:39][C:38]([CH3:40])=[N:37][N:36]=3)[CH2:31][S:32][C@H:27]12)=[O:24]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 54432-Mercaptobenzoic AcidHCID 31398ChlorosuccinimideHCID 88734110HCID 88734110, compound

Product 1

HCID 88784322HCID 88784322, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

While a mixed solution of 0.462 g thiosalicylic acid and 0.6 g triethylamine in 8 ml of methylene chloride is cooled with ice, 0.4 g of N-chlorosuccinimide is added. The mixture is stirred for 5 minutes. Separately, a solution of 1 g 7-(4-chloro-3-oxobutyrylamino)-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid and 0.6 g triethylamine in 15 ml of methylene chloride is ice-cooled and the above reaction mixture is added at one time and stirred for 2 minutes. This reaction mixture is stirred vigorously with 3 ml of 50% phosphoric acid and 7 ml of saturated aqueous sodium chloride. The organic layer is taken and the water layer is extracted with ethyl acetate. The organic layers are combined and dried. The solvent is then distilled off under reduced pressure and the residue is stirred with ether. By the above procedure is obtained 7-[4-chloro-3-oxo-2-(2-carboxyphenylthio)butyrylamino]-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid as powders. Yield 1.4 g. IR (KBr, cm-1): 1770, 1700, 1590, 1520, 1380, 1230, 750 NMR (90 MHz, d6 -DMSO, δ): 2.67(s, thiadiazole--CH3), 3.40 & 3.67(ABq, J=18 Hz, 2--CH2), 4.17 & 4.52(ABq, J=13.5 Hz, 3--CH2), 4.48(s, ClCH2CO), 5.02(d, J=4.5 Hz, 6--H), 5.58(dd, J=4.5, 9.0 Hz, 7H), 8.67(d, J=9 Hz, CONH--)

Workup

  1. additionis added
  2. temperaturecooled
  3. additionthe above reaction mixture is added at one time
  4. stirringstirred for 2 minutes
  5. extractionthe water layer is extracted with ethyl acetate
  6. customdried
  7. distillationThe solvent is then distilled off under reduced pressure
  8. stirringthe residue is stirred with ether

Sources & evidence

ORD record
ord-25d6815ce4924d9c8d7de70cda0b2f94
Source dataset
uspto-grants-1980_12
Patent number
US04238608

Reaction notes

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