Dicyclohexylcarbodiimide → HCID 16166029, compound

HRID 2352087Notes

Reaction equation

HRID 2352087 reaction equation
ON1C2C=CC=CC=2N=N1.[C:11]([NH:30][C:31]1[S:32][CH:33]=[C:34](/[C:36](=[N:40]/[O:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)/[C:37](O)=[O:38])[N:35]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:76][CH:77]1[C:107](=[O:108])[N:79]2[C:80]([C:91]([O:93][CH:94]([C:101]3[CH:106]=[CH:105][CH:104]=[CH:103][CH:102]=3)[C:95]3[CH:100]=[CH:99][CH:98]=[CH:97][CH:96]=3)=[O:92])=[C:81](/[CH:84]=[CH:85]/[CH2:86][O:87][C:88](=[O:90])[CH3:89])[CH2:82][S:83][C@H:78]12>C1COCC1>[C:11]([NH:30][C:31]1[S:32][CH:33]=[C:34](/[C:36](=[N:40]/[O:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)/[C:37]([NH:76][CH:77]2[C:107](=[O:108])[N:79]3[C:80]([C:91]([O:93][CH:94]([C:95]4[CH:96]=[CH:97][CH:98]=[CH:99][CH:100]=4)[C:101]4[CH:106]=[CH:105][CH:104]=[CH:103][CH:102]=4)=[O:92])=[C:81](/[CH:84]=[CH:85]/[CH2:86][O:87][C:88](=[O:90])[CH3:89])[CH2:82][S:83][C@H:78]23)=[O:38])[N:35]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10327150(Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic AcidHCID 15017680HCID 15017680, compound

Product 1

HCID 16166029HCID 16166029, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 1-hydroxybenzotriazole (223 mg, 1.44 mmol) and (Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetic acid (1.06 g, 1.44 mmol) in THF (14 ml) was added DCC (300 mg, 1.44 mmol) and the mixture was stirred for 1 hr at 5° C. Diphenylmethyl 7-amino-3-[(E)-acetoxy-1-propenyl]-3-cephem-4-carboxylate (670 mg, 1.44 mmol) was added to the mixture. After stirring for 4 hr at ambient temperature, the reaction mixture was filtered, diluted with ethyl acetate (50 ml) and washed with water. Concentration of the organic layer gave an oil, which was chromatographed on a column of silica gel. Elution with toluene-ethyl acetate (10:1) gave 1.607 g (99%) of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(E)-3-acetoxy-1-propenyl]-3-cephem-4-carboxylate as an amorphous powder. IR νmax (KBr) cm-1 1770, 1730. 1H NMR (CDCl3) δ 2.0 (3H, s, OAc), 3.33 (2H, s, 2-H), 4.54 (2H, ABq, CH2OAc), 5.04 (1H, d, J=5 Hz, 6-H), 6.0 (1H, m, vinyl-H), 6.02 (1H, dd, J=5 & 7 Hz, 7-H), 6.40 (1H, s, thiazole-H), 6.82 (1H, d, J=15 Hz, vinyl-H), 7.00 (1H, s, Ph2CH), 7.3 (25H, s, Ph).

Workup

  1. stirringAfter stirring for 4 hr at ambient temperature
  2. filtrationthe reaction mixture was filtered
  3. additiondiluted with ethyl acetate (50 ml)
  4. washwashed with water
  5. customConcentration of the organic layer gave an oil, which
  6. customwas chromatographed on a column of silica gel
  7. washElution with toluene-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-62ea78afe6ff4fb0b73ade328bec7d26
Source dataset
uspto-grants-1989_10
Patent number
US04874856

Reaction notes

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