Hydrochloric Acid → Diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate

HRID 1904121Notes

Reaction equation

HRID 1904121 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:65])[C:32]([C:40]3[N:41]=[C:42]([NH:45][C:46]([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[S:43][CH:44]=3)=[N:33][O:34]C(C)(OC)C)[C:28](=[O:66])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].Cl>CC(C)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:65])[C:32]([C:40]3[N:41]=[C:42]([NH:45][C:46]([C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=4)([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[S:43][CH:44]=3)=[N:33][OH:34])[C:28](=[O:66])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131712392Diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate

Product 1

HCID 131712161Diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.775 g of the product of Step A, 14 ml of acetone and 4.5 ml of N hydrochloric acid was stirred for 2 hours at room temperature and the acetone was evaporated under reduced pressure. 20 ml of ethyl acetate were added thereto and the mixture was stirred and decanted. The organic phase was washed 4 times with 10 ml of slightly salted water and the wash waters were extracted with 5 ml of ethyl acetate. The combined organic phases were dried and vacuum filtered and the filter was rinsed with ethyl acetate. The filtrate was evaporated to dryness under reduced pressure and the residue was taken up in ether and was crystallized. Efflorescence occurred and the mixture was vacuum filtered. The product was rinsed with ether and was dried to obtain 1.88 g of the syn isomer of diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate with a Rf=0.5 (eluant-ether containing 20% acetone).

Workup

  1. customthe acetone was evaporated under reduced pressure
  2. addition20 ml of ethyl acetate were added
  3. stirringthe mixture was stirred
  4. customdecanted
  5. washThe organic phase was washed 4 times with 10 ml of slightly salted water
  6. extractionthe wash waters were extracted with 5 ml of ethyl acetate
  7. customThe combined organic phases were dried
  8. filtrationvacuum filtered
  9. washthe filter was rinsed with ethyl acetate
  10. customThe filtrate was evaporated to dryness under reduced pressure
  11. customwas crystallized
  12. filtrationfiltered
  13. washThe product was rinsed with ether
  14. customwas dried

Sources & evidence

ORD record
ord-d0f64c919c72482e8a0e26fd353b2c8c
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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