Dicyclohexylcarbodiimide → HCID 131712193, compound

HRID 1703032Notes

Reaction equation

HRID 1703032 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][C:17]1([O:50][CH3:51])[C:48](=[O:49])[N:19]2[C:20]([C:32]([O:34][CH:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])=[C:21]([CH2:24][S:25][C:26]3[N:30]([CH3:31])[N:29]=[N:28][N:27]=3)[CH2:22][S:23][C@H:18]12.[CH3:52][O:53][N:54]=[C:55]([C:59]1[N:60]=[N:61][S:62][CH:63]=1)[C:56](O)=[O:57]>O1CCCC1>[CH3:52][O:53][N:54]=[C:55]([C:59]1[N:60]=[N:61][S:62][CH:63]=1)[C:56]([NH:16][C:17]1([O:50][CH3:51])[C:48](=[O:49])[N:19]2[C:20]([C:32]([O:34][CH:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:33])=[C:21]([CH2:24][S:25][C:26]3[N:30]([CH3:31])[N:29]=[N:28][N:27]=3)[CH2:22][S:23][C@H:18]12)=[O:57]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12882024HCID 12882024, compoundHCID 543473402-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid

Product 1

HCID 131712193HCID 131712193, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dicyclohexylcarbodiimide (0.99 g.) was added at ambient temperature to a solution of diphenylmethyl 7-amino-7-methoxy-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate (2.1 g.) in dry tetrahydrofuran (20 ml.) and then 2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid (syn isomer) (0.9 g) was added thereto at ambient temperature to give white precipitates. After stirring for 2 days at ambient temperature, the precipitates were filtered off and the filtrate was concentrated under reduced pressure to give brown oil. The oil was subjected to column chromatography on silica gel, eluted with a mixture of chloroform and ethyl acetate and the eluate was concentrated under reduced pressure to give diphenylmethyl 7-[2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetamido]-7-methoxy-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (1.78 g.).

Workup

  1. customat ambient temperature to give white precipitates
  2. filtrationthe precipitates were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give brown oil
  5. washeluted with a mixture of chloroform and ethyl acetate
  6. concentrationthe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dfcaae2e66df47f6866ef999d3c36e6a
Source dataset
uspto-grants-1982_09
Patent number
US04350693

Reaction notes

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