Dicyclohexylcarbodiimide → HCID 178491510, compound

HRID 1461168Notes

Reaction equation

HRID 1461168 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)/[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:38][CH:39]1[C:65](=[O:66])[N:41]2[C:42]([C:53]([O:55][CH2:56][C:57]3[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][CH:58]=3)=[O:54])=[C:43](/[CH:46]=[CH:47]\[C:48]3[N:49]=[N:50][S:51][CH:52]=3)[CH2:44][S:45][C@H:40]12.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)/[C:27]([NH:38][CH:39]2[C:65](=[O:66])[N:41]3[C:42]([C:53]([O:55][CH2:56][C:57]4[CH:58]=[CH:59][C:60]([O:63][CH3:64])=[CH:61][CH:62]=4)=[O:54])=[C:43](/[CH:46]=[CH:47]\[C:48]4[N:49]=[N:50][S:51][CH:52]=4)[CH2:44][S:45][C@H:40]23)=[O:28])[N:25]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14071104HCID 14071104, compoundHCID 14621694HCID 14621694, compound

Product 1

HCID 178491510HCID 178491510, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Z)-2-(2-tritylaminothiazol-4-yl)-2-tetrahydropyranyloxyiminoacetic acid (0.39 g, 0.76 mmol) and p-methoxybenzyl 7-amino-3-[(Z)-2-(1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (1.33 g, 0.76 mmol) were dissolved in methylene chloride (10 ml) and stirred at room temperature for 12 hours by addition of DCC (0.18 g, 0.87 mmol). Insolubles were filtered and then the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography thereby p-methoxybenzyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-tetrahydropyranyloxyiminoacetamido]-3-[(Z)-2-(1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (0.25 g) was obtained as a light yellow powder compound.

Workup

  1. filtrationInsolubles were filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-96414e54e4ef4a60a21e7510bdb15525
Source dataset
uspto-grants-1991_12
Patent number
US05073551

Reaction notes

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