Pyridine → HCID 13367930, compound

HRID 1153933Notes

Reaction equation

HRID 1153933 reaction equation
C([O:5][C:6]([C:8]([O:11]/[N:12]=[C:13](/[C:46]1[N:47]=[C:48]([NH:51]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:49][CH:50]=1)\[C:14]([NH:16][CH:17]1[C:44](=[O:45])[N:19]2[C:20]([C:28]([O:30]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:29])=[C:21]([CH:24]=[CH:25][CH2:26]I)[CH2:22][S:23][C@H:18]12)=[O:15])([CH3:10])[CH3:9])=[O:7])(C)(C)C.[N:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1>ClCCl.C(OC(C)C)(C)C>[NH2:51][C:48]1[S:49][CH:50]=[C:46](/[C:13](=[N:12]/[O:11][C:8]([C:6]([OH:7])=[O:5])([CH3:10])[CH3:9])/[C:14]([NH:16][CH:17]2[C:44](=[O:45])[N:19]3[C:20]([C:28]([O-:30])=[O:29])=[C:21](/[CH:24]=[CH:25]/[CH2:26][N+:71]4[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[N:47]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 172930624HCID 172930624, compound

Product 1

HCID 13367930HCID 13367930, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(2-t-butoxycarbonyl-2-propoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (X-4', 497 mg, 0.5 mmole) and pyridine (0.08 ml, 1 mmole) in dichloromethane (5 ml) was allowed to stand at room temperature for 3.5 hours, and was then diluted with diisopropyl ether. The resulting precipitate was collected by filtration and treated with trifluoroacetic acid (5 ml) and anisole (1 ml) at room temperature for 1 hour, and the resulting mixture was concentrated and triturated with ether to give crude product I-4B which was purified by HP-20 column chromatography, eluted with water (300 ml), 10% methanol (500 ml) and 30% methanol (300 ml). The eluate of 30% methanol was concentrated to a small volume, adjusted to pH 7 with sodium bicarbonate and lyophilized to afford 23 mg (7%) of the title compound I-4B. M.p. >150° C.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. additiontreated with trifluoroacetic acid (5 ml) and anisole (1 ml) at room temperature for 1 hour
  3. concentrationthe resulting mixture was concentrated
  4. customtriturated with ether
  5. customto give crude product I-4B which
  6. customwas purified by HP-20 column chromatography
  7. washeluted with water (300 ml), 10% methanol (500 ml) and 30% methanol (300 ml)
  8. concentrationThe eluate of 30% methanol was concentrated to a small volume

Sources & evidence

ORD record
ord-5382e2bb423649088089b08c9d8f181c
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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