4-Phenylsemicarbazide hydrochloride → 6,9-Dihydroxy-4-(4-phenylsemicarbazonomethyl)-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-8-ylmethyl carbamate

HRID 1252443Notes

Reaction equation

HRID 1252443 reaction equation
[C:1](=[O:23])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[NH:15]3)[C:11]2[C:6]1=[C:7]([OH:22])[CH:8]=[C:9]([CH:20]=O)[CH:10]=2)[NH2:2].C(=O)(O)[O-].[Na+].Cl.[C:30]1([NH:36][C:37](=[O:40])[NH:38][NH2:39])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO>[C:1](=[O:23])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[NH:15]3)[C:11]2[C:6]1=[C:7]([OH:22])[CH:8]=[C:9]([CH:20]=[N:39][NH:38][C:37]([NH:36][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:40])[CH:10]=2)[NH2:2]

Participants

5

Reactant 3

HCID 795054-Phenylsemicarbazide hydrochlorideHCID 516892Sodium BicarbonateHCID 10448726(4-Formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-trien-8-yl)methyl carbamate

Product 1

HCID 571957506,9-Dihydroxy-4-(4-phenylsemicarbazonomethyl)-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-8-ylmethyl carbamateYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (50 mg) in methanol (5 ml) were added sodium bicarbonate (27 mg) and 4-phenylsemicarbazide hydrochloride (59 mg). The mixture was stirred for 1 hour at ambient temperature and evaporated in vacuo. The residue was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (3:1, v/v) to afford 6,9-dihydroxy-4-(4-phenylsemicarbazonomethyl)-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (64 mg).

Workup

  1. customevaporated in vacuo
  2. additionwas developed with a mixture of chloroform and methanol (3:1

Sources & evidence

ORD record
ord-d1bd518c4a674fc4a993d4a5d2382278
Source dataset
uspto-grants-1988_05
Patent number
US04743555

Reaction notes

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