Phosphoric Acid → Tamiflu

HRID 2194853

Reaction equation

HRID 2194853 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@H:10]([NH2:12])[C@@H:9]([NH:13][C:14](=[O:16])[CH3:15])[C@H:8]([O:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:7]=1)=[O:5])[CH3:2].[P:23](=[O:27])([OH:26])([OH:25])[OH:24]>>[P:23]([OH:27])([OH:26])([OH:25])=[O:24].[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@H:10]([NH2:12])[C@@H:9]([NH:13][C:14](=[O:16])[CH3:15])[C@H:8]([O:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 1004Phosphoric AcidHCID 65028Oseltamivir

Product 1

HCID 78000Tamiflu

Procedure

Form B may be formed by adding (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester to the phosphoric acid and cooling the supersaturated solution from 50° C. to −40° C. as fast as possible (without seeding).

Workup

  1. customForm B may be formed
  2. temperaturecooling the supersaturated solution from 50° C. to −40° C. as fast as possible (without seeding)

Sources & evidence

ORD record
ord-0c10069f60fc4ba9a6e569cad3915ad6
Source dataset
uspto-grants-2012_12
Patent number
US08334319B2

Linked notes

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