Camptothecin → HCID 4442037, compound

HRID 720490Notes

Reaction equation

HRID 720490 reaction equation
[BH4-].[Na+].[CH3:3][CH2:4][C@@:5]1([OH:28])[C:10](=[O:11])[O:9][CH2:8][C:7]2[C:12]([N:14]3[C:26](=[CH:27][C:6]1=2)[C:25]1[C:16](=[CH:17][C:18]2[C:23]([N:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15]3)=[O:13]>CO>[CH2:4]([C:5]1([OH:28])[C:6]2[CH:27]=[C:26]3[N:14]([CH2:15][C:16]4[C:25]3=[N:24][C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH:17]=4)[C:12](=[O:13])[C:7]=2[CH2:8][O:9][CH:10]1[OH:11])[CH3:3]

Participants

4

Reactant 2

HCID 24360CamptothecinHCID 4311764Sodium borohydride

Product 1

HCID 4442037HCID 4442037, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (14 g, 370 mmol) is added by portions to a suspension of (S)-(+)-camptothecin (14 g, 40 mmol, which can be obtained from different commercial sources such as Aldrich Chemical Co. (Milwaukee, Wis.)), in methanol (750 ml) and the resultant mixture is heated gently to 55° C. in order to obtain a limpid solution which is then agitated for 16 hours at ambient temperature. The solvent is then evaporated off under reduced pressure, the residue is taken up in water (250 ml), neutralized by the addition of acetic acid (21 ml) and left at rest for 2 hours at 4° C. The resultant suspension is filtered and washed successively with cold water, acetone and diethyl ether, which allows the sought product to be obtained, after drying under reduced pressure, in the form of a white solid m.p. 280° C.

Workup

  1. customto obtain a limpid solution which
  2. customThe solvent is then evaporated off under reduced pressure
  3. additionneutralized by the addition of acetic acid (21 ml)
  4. waitleft at rest for 2 hours at 4° C
  5. filtrationThe resultant suspension is filtered
  6. washwashed successively with cold water, acetone and diethyl ether, which
  7. customto be obtained
  8. dry with materialafter drying under reduced pressure, in the form of a white solid m.p. 280° C.

Sources & evidence

ORD record
ord-e18cd7330f594343bd68cd71a19f6883
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

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