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p-Toluenesulfonic acid → Cositecan

HRID 1024329
Notes
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Reaction equation

HRID 1024329 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:27][CH2:28][C@@:29]1([OH:58])[C:34](=[O:35])[O:33][CH2:32][C:31]2[C:36]([N:38]3[C:50](=[CH:51][C:30]1=2)[C:49]1N=C2C(C(CC[Si](C)(C)C)=CC=C2)=C[C:40]=1[CH2:39]3)=[O:37]>C(O)(=O)C.C1(C)C=CC=CC=1>[CH3:27][CH2:28][C@@:29]1([OH:58])[C:34](=[O:35])[O:33][CH2:32][C:31]2[C:36]([N:38]3[C:50](=[CH:51][C:30]1=2)[C:49]1[C:40](=[C:8]([CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]2[C:2]([N:1]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:39]3)=[O:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 54580717HCID 54580717, compoundHCID 86718835HCID 86718835, compound

Product 1

HCID 148202CositecanYield 98%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 1140
Toluene
Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(2-amino-phenyl)-3-trimethylsilanyl-propan-1-one (3) (34 mg) and CDE ring moiety (4) (24 mg) in acetic acid (0.5 mL) and toluene (1 mL) was added p-toluenesulfonic acid (1 mg). The reaction solution was stirred for 20 hours at 100° C. After cooling to room temperature, the reaction solution was concentrated under reduced pressure and the residue was washed with hexane (10 mL), water (10 mL), and a mixture of acetone (5 mL) and hexane (5 mL). The yellow solid was evaporated to dryness in vacuo to yield 39 mg (98% Yield) of BNP1350 (Karenitecin; Cositecan; 7-(2′-trimethylsilyl)ethyl camptothecin; IUPAC Nomenclature: (4S)-4-ethyl-4-hydroxy-11-[2-(trimethylsilyl)ethyl]-1H-pyrano[3′:4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. washthe residue was washed with hexane (10 mL), water (10 mL)
  4. additiona mixture of acetone (5 mL) and hexane (5 mL)
  5. customThe yellow solid was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5bce4e5af9ea4870a0247770e7197424
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722886B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes