HCID 14084036, compound → Cephalotaxine

HRID 1166459Notes

Reaction equation

HRID 1166459 reaction equation
[CH3:1][O:2][C:3]1[C@@H:19]([OH:20])[C@@H:18]2[C@:5]3([N:9]([CH2:10][CH2:11][C:12]4[C:17]2=[CH:16][C:15]2[O:21][CH2:22][O:23][C:14]=2[CH:13]=4)[CH2:8][CH2:7][CH2:6]3)[CH:4]=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C@@H:19]([OH:20])[C@@H:18]2[C@@:5]3([N:9]([CH2:10][CH2:11][C:12]4[C:17]2=[CH:16][C:15]2[O:21][CH2:22][O:23][C:14]=2[CH:13]=4)[CH2:8][CH2:7][CH2:6]3)[CH:4]=1

Participants

3

Reactant 1

HCID 14084036HCID 14084036, compound

Product 1

HCID 65305Cephalotaxine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Batch A: 1H NMR 400 MHz (CDCl3) (d ppm): 6.06 (1H, OCH2O (+)-cephalotaxine) and 5.82 (1H, OCH2O (+)-cephalotaxine); 5.99 (1H, OCH2O (−)-cephalotaxine) and 5.76 (1H, OCH2O (−)-cephalotaxine). Presence of 11±5% de (+)-cephalotaxine. [a]22=−134,02° (c=0,214; CHCl3): calculated rate 25±5% Batch B: slightly racemized (1%) [a]19=−173,3° (c=0,208; CHCl3)

Sources & evidence

ORD record
ord-4e6a98fc48df46a7b7f1bb534a03fbe3
Source dataset
uspto-grants-2003_09
Patent number
US06613900B2

Reaction notes

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