Dicyclohexylcarbodiimide → HCID 178442197, compound

HRID 979387Notes

Reaction equation

HRID 979387 reaction equation
Cl.[NH2:2][C@@H:3]1[C:31](=[O:32])[N:5]2[C:6]([C:15]([O:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])=[C:7](/C=C/C#CC)[CH2:8][S:9][C@H:4]12.[C:33]([CH2:36][O:37]/[N:38]=[C:39](/[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[S:46][CH:47]=1)\[C:40]([OH:42])=O)(=[O:35])[NH2:34].O.ON1[C:74]2[CH:75]=C[CH:77]=[CH:78][C:73]=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(N(CC)CC)C>[C:33]([CH2:36][O:37]/[N:38]=[C:39](/[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[S:46][CH:47]=1)\[C:40]([NH:2][C@@H:3]1[C:31](=[O:32])[N:5]2[C:6]([C:15]([O:17][CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:16])=[CH:7][CH:8](/[CH:75]=[CH:74]/[C:73]#[C:78][CH3:77])[S:9][C@H:4]12)=[O:42])(=[O:35])[NH2:34]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12816813(2Z)-2-(2-amino-2-oxoethoxy)imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acidHCID 131715146diphenylmethyl(6R,7R)-7-amino-3-[(E)-pent-1-en-3-ynyl]ceph-3-em-4-carboxylate, hydrochloride

Product 1

HCID 178442197HCID 178442197, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A stirred solution of diphenylmethyl(6R,7R)-7-amino-3-[(E)-pent-1-en-3-ynyl]ceph-3-em-4-carboxylate, hydrochloride (432 mg) in tetrahydrofuran (10 ml) was treated with triethylamine (125 μl). (Z)-2-(Carbamoylmethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (441 mg), 1-hydroxybenzotriazole hydrate (162 mg) and N,N'-dicyclohexylcarbodiimide (248 mg) were added in that order. After 3 h, the precipitated N,N'-dicyclohexylurea was filtered off, the filtrate evaporated and the residue purified by column chromatography (60 g silica gel). Elution with ethyl acetate:dichloromethane (1:3) gave the title compound as a foam (441 mg); νmax (CHBr3) 3500, 3398 (NH2 +NH), 2215 (C≡C), 1786 (β-lactam), 1722 (CO2R), 1682, 1528 cm-1 (CONH); τ(CDCl3) 4.24 (CH=CH--C≡C), 5.33 (OCH2CONH2), 6.48, 6.60 (2-CH2), 8.02 (C≡CCH 3).

Workup

  1. filtrationthe precipitated N,N'-dicyclohexylurea was filtered off
  2. customthe filtrate evaporated
  3. customthe residue purified by column chromatography (60 g silica gel)
  4. washElution with ethyl acetate:dichloromethane (1:3)

Sources & evidence

ORD record
ord-efb420cb9d8745abb8fb8a0d26a4243e
Source dataset
uspto-grants-1987_05
Patent number
US04666899

Reaction notes

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