Ammonium Hydroxide → Vincristine

HRID 542923Notes

Reaction equation

HRID 542923 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:60])[CH2:19][N:18]2[CH2:20][CH2:21][C@@:16]34[C@@H:17]2[C@@H:5]([CH2:6][C@:7]([C:56]([O:58][CH3:59])=[O:57])([C:22]2[CH:27]=[C:26]5[C@@:28]67[C@@H:39]([N:40]([CH:41]=[O:42])[C:25]5=[CH:24][C:23]=2[O:54][CH3:55])[C@@:38]([OH:47])([C:43]([O:45][CH3:46])=[O:44])[C@H:37]([O:48][C:49]([CH3:51])=[O:50])[C@:33]2([CH2:52][CH3:53])[CH:34]=[CH:35][CH2:36][N:31]([C@H:32]62)[CH2:30][CH2:29]7)[C:8]3=[N:9][C:10]2[C:15]4=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.[BH4-].[Na+].[OH-].[NH4+]>C(O)(=O)C>[CH3:1][CH2:2][C@@:3]1([OH:60])[CH2:19][N:18]2[CH2:17][C@@H:5]([CH2:6][C@:7]([C:56]([O:58][CH3:59])=[O:57])([C:22]3[CH:27]=[C:26]4[C@:28]56[C@@H:32]7[C@:33]([CH2:52][CH3:53])([C@@H:37]([O:48][C:49]([CH3:51])=[O:50])[C@:38]([OH:47])([C:43]([O:45][CH3:46])=[O:44])[C@@H:39]5[N:40]([CH:41]=[O:42])[C:25]4=[CH:24][C:23]=3[O:54][CH3:55])[CH:34]=[CH:35][CH2:36][N:31]7[CH2:30][CH2:29]6)[C:8]3[NH:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:16]=3[CH2:21][CH2:20]2)[CH2:4]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 100953811HCID 100953811, compound

Product 1

HCID 5978Vincristine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To the solution of 53 mg (0.06 mmole) cyclovincristine in 5 ml abs. glacial acetic acid an excess of sodium borohydride (ca. 40 mg) is added in portions at ambient temperature. The reaction is controlled by TLC (Merck Kieselgel 60F254, Rf of starting material>Rf of product). When the reaction has been completed (ca. 2-3 hours at 25° C.), the solution is poured onto ice-water, rendered alkaline with concentrated aqueous ammonium hydroxide solution to pH 9, then extracted with 2×20 ml of dichloromethane. The combined organic phase is washed with 2×15 ml of water, dried (MgSO4) and evaporated in vacuo. The crude product obtained is purified by preparative chromatography (Kieselgel PF254+366).

Workup

  1. custom(ca. 2-3 hours at 25° C.)
  2. additionthe solution is poured onto ice-water
  3. extractionextracted with 2×20 ml of dichloromethane
  4. washThe combined organic phase is washed with 2×15 ml of water
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f166e45ecc04fbaa0cd985b1fa4820b
Source dataset
uspto-grants-1987_04
Patent number
US04659816

Reaction notes

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