Hydrochloric Acid → HCID 69318042, compound

HRID 1393371Notes

Reaction equation

HRID 1393371 reaction equation
C[O:2][C:3](=[O:43])[C@H:4]([CH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH2:21][CH2:22][C:23]2[N:24]=[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34]CC4C=CC=CC=4)[CH:29]=3)[O:26][CH:27]=2)=[C:15]([Cl:42])[CH:14]=1)[NH:5]C(=O)C(F)(F)F.Cl>C(O)(=O)C>[Cl:19][C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([Cl:42])[C:16]=1[O:20][CH2:21][CH2:22][C:23]1[N:24]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)[O:26][CH:27]=1)[CH2:12][C@@H:4]([C:3]([OH:43])=[O:2])[NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86598314HCID 86598314, compound

Product 1

HCID 69318042HCID 69318042, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of O-[2-[2-(3-benzyloxyphenyl)-oxazol-4-yl]ethyl]-3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester (316 mg, 0.496 mmol), hydrochloric acid (3 ml) and acetic acid (1.5 ml) was heated under reflux for 6 hrs. The reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. Water (30 ml) was added to the residue and the mixture was adjusted to pH 4-5 with 10% aqueous sodium hydroxide. The precipitates were collected by filtration, washed with water, suspended in ethanol (20 ml) and triturated. The resultant product was collected by filtration, washed with ethanol and dried under reduced pressure to give 3,5-dichloro-O-[2-[2-(3-hydroxyphenyl)-oxazol-4-yl]ethyl]-L-tyrosine (115 mg, 52%) as a pale brown solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hrs
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater (30 ml) was added to the residue
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. customtriturated
  8. filtrationThe resultant product was collected by filtration
  9. washwashed with ethanol
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-d457737ec4a24bc8b08b48eb81c2bb38
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

Loading…