4-Hydroxyphenylglycine → Oxfenicine

HRID 328170Notes

Reaction equation

HRID 328170 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:4][CH:3]=1>C(O)C>[CH:4]1[C:5]([C@H:8]([NH2:9])[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

3

Reactant 1

HCID 921434-Hydroxyphenylglycine

Product 1

HCID 36143Oxfenicine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of DL-2-(4-hydroxyphenyl)glycine (10 g.), d-3-bromo-2-oxo-10-bornanesulfonic acid (20 g.) and hot 99% ethanol (100 ml.) was filtered, and the filtrate was concentrated under reduced pressure to a total weight of 40 g. Chloroform (265 g.) was added to the solution, and the solution was seeded with the authentic specimen of d-3-bromo-2-oxo-10-bornanesulfonic acid salt of L-2-(4-hydroxyphenyl)glycine and allowed to stand for 2 hours at room temperature. The precipitating crystals were collected by filtration, washed with a mixture of ethanol and chloroform (5 : 1) and dried for 12 hours at room temperature under reduced pressure to give the solvate (16.1 g.) of d-3-bromo-2-oxo-10-bronanesulfonic acid salt of L-2-(4-hydroxyphenyl)glycine with chloroform. Recrystallization from a mixture of ethanol (20 g.) and chloroform (250 g.) in a similar manner to the above gave the pure solvate (15.1 g.), m.p. 190° to 197° C. The differential thermal analysis of this solvate gave the endothermic peak at 155° to 156° C.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated under reduced pressure to a total weight of 40 g
  3. additionChloroform (265 g.) was added to the solution
  4. filtrationThe precipitating crystals were collected by filtration
  5. washwashed with a mixture of ethanol and chloroform (5 : 1)
  6. customdried for 12 hours at room temperature under reduced pressure

Sources & evidence

ORD record
ord-5beed8231c1d4c209370135f2661b095
Source dataset
uspto-grants-1977_04
Patent number
US04016205

Reaction notes

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