Camptothecin → HCID 11024585, compound

HRID 1084458Notes

Reaction equation

HRID 1084458 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11]>CC(O)=O.O=[Pt]=O>[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[CH:23]1[CH:14]([CH2:15][C:16]2[C:21]([NH:22]1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]

Participants

4

Reactant 1

HCID 24360Camptothecin

Product 1

HCID 11024585HCID 11024585, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent2×

Procedure

Camptothecin (32.0 g, 0.092 mol.) obtained from Tainjain-SK&F Ltd., Tainjain, China, was combined with Pt0 [prepared by pre reduction of 8.0 g. amorphous PtO2 in 800 mL HOAc for 1.5 hour (h) under 1 atmosphere (atm.) H2 ] and HOAc (1.6 L). Reduction was carried out at 1 atm. H2 for 8.5 h. while vigorously stirring the mixture. At the end of this time, the theoretical amount of H2 had been absorbed (slightly more than 4.1 L) and the uptake of H2 had slowed considerably. The reaction was degassed with a stream of Ar for approximately 10 minutes (min.), and then filtered through a celite pad which was washed with HOAc (200 mL).

Workup

  1. customprepared by pre reduction of 8.0 g
  2. customAt the end of this time, the theoretical amount of H2 had been absorbed (slightly more than 4.1 L) and the uptake of H2
  3. customThe reaction was degassed with a stream of Ar for approximately 10 minutes (min.)
  4. filtrationfiltered through a celite pad which
  5. washwas washed with HOAc (200 mL)

Sources & evidence

ORD record
ord-99aacc8ebc1e44f2af07487614c5e8a9
Source dataset
uspto-grants-1991_04
Patent number
US05004758

Reaction notes

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