Pyridine → HCID 13453761, compound

HRID 1153934Notes

Reaction equation

HRID 1153934 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:11][C:12]([C:14]1([O:18]/[N:19]=[C:20](/[C:53]2[N:54]=[C:55]([NH:58]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:56][CH:57]=2)\[C:21]([NH:23][CH:24]2[C:51](=[O:52])[N:26]3[C:27]([C:35]([O:37]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:36])=[C:28]([CH:31]=[CH:32][CH2:33]I)[CH2:29][S:30][C@H:25]23)=[O:22])[CH2:17][CH2:16][CH2:15]1)=[O:13])(C)(C)C>ClCCl.C(OC(C)C)(C)C>[NH2:58][C:55]1[S:56][CH:57]=[C:53](/[C:20](=[N:19]/[O:18][C:14]2([C:12]([OH:13])=[O:11])[CH2:17][CH2:16][CH2:15]2)/[C:21]([NH:23][CH:24]2[C:51](=[O:52])[N:26]3[C:27]([C:35]([O-:37])=[O:36])=[C:28](/[CH:31]=[CH:32]/[CH2:33][N+:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:29][S:30][C@H:25]23)=[O:22])[N:54]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 172930626HCID 172930626, compound

Product 1

HCID 13453761HCID 13453761, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

Pyridine (0.1 ml, 1.2 mmole) was added to a solution of diphenylmethyl 7-[(Z)-2-(1-t-butoxycarbonylcyclobut-1-oxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (X-5', 659 mg, 9.6 mmole) in dichloromethane (7 ml). The mixture was stirred at room temperature for 2.5 hours and diluted with diisopropyl ether. The resulting solid (383 mg) was collected by filtration and treated with 90% trifluoroacetic acid (5 ml) and anisole (1 ml) at room temperature for 1 hour. The resulting mixture was concentrated and the residue was triturated with ether to give 237 mg of crude I-5B, which was purified by HP-20 column chromatography [eluted with water (150 ml), 10% methanol (200 ml) and 30% methanol (500 ml)]. The eluate of 30% methanol was concentrated to a small volume, adjusted to pH 7 with sodium bicarbonate and lyophilized to afford 72 mg (21%) of I-5B. M.P. >160° C. (dec.).

Workup

  1. filtrationThe resulting solid (383 mg) was collected by filtration
  2. additiontreated with 90% trifluoroacetic acid (5 ml) and anisole (1 ml) at room temperature for 1 hour
  3. concentrationThe resulting mixture was concentrated
  4. customthe residue was triturated with ether
  5. customto give 237 mg of crude I-5B, which
  6. customwas purified by HP-20 column chromatography [eluted with water (150 ml), 10% methanol (200 ml) and 30% methanol (500 ml)]
  7. concentrationThe eluate of 30% methanol was concentrated to a small volume
  8. customto afford 72 mg (21%) of I-5B

Sources & evidence

ORD record
ord-d0aa0952b13140c38991da0185f49deb
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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