Acetic Acid → HCID 86733421, compound

HRID 1076472Notes

Reaction equation

HRID 1076472 reaction equation
C[C@@H]1O[C@@H](O[C@@H:9]2[C:14]3=[C:15](O)[C:16]4[C:28](=O)[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5OC)[C:20](=O)[C:17]=4[C:18](O)=[C:13]3[CH2:12][C@@:11](O)(C(C)=O)[CH2:10]2)C[C@H](N)[C@@H]1O.[ClH:39].C(O)(=O)C.[NH2:44][NH:45][C:46]([NH2:48])=[S:47]>C(O)C>[ClH:39].[N:44](=[C:20]1[C:17]2[C:16](=[CH:15][C:14]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[CH:18]=2)[CH2:28][C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]1=2)[NH:45][C:46]([NH2:48])=[S:47]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 62770Daunorubicin HydrochlorideHCID 2723789Thiosemicarbazide

Product 1

HCID 86733421HCID 86733421, compoundYield 187.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Daunorubicin hydrochloride (0.4 g.) is dissolved in ethanol (60 cc.) containing 2.5% of acetic acid, and thiosemicarbazide (0.135 g.) is then added. The resulting mixture is heated for 12 hours to 45°C. with stirring, then evaporated to dryness under reduced pressure, and the residue is taken up in water (50 cc.). The resulting solution is lyophilized to give 4-methoxy-5- (or 12-) oxo-6,9,11-trihydroxy-7-(2,3,6-O-tridesoxy-3-amino-1-L-lyxohexosyl)-9-[1-(thiosemicarbazono)ethyl]-12- (or 5-) (thiosemicarbazono)-5,7,8,9,10,12-hexahydro-naphthacene hydrochloride (0.476 g.) in a yield of 89%.

Workup

  1. additionis then added
  2. temperatureThe resulting mixture is heated for 12 hours to 45°C.
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8a2a56ede7a0423cada08cf90d0bd685
Source dataset
uspto-grants-1976_05
Patent number
US03957755

Reaction notes

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