Acetic Acid → HCID 69328059, compound

HRID 1393375Notes

Reaction equation

HRID 1393375 reaction equation
C[O:2][C:3](=[O:34])[C@H:4]([CH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:31]C)[CH:27]=3)[CH:22]=2)=[C:15]([Cl:33])[CH:14]=1)[NH:5]C(=O)C(F)(F)F.Br.C(O)(=O)C.[OH-].[Na+]>O>[Cl:19][C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([Cl:33])[C:16]=1[O:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([OH:31])[CH:27]=2)[CH:22]=1)[CH2:12][C@@H:4]([C:3]([OH:34])=[O:2])[NH2:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 87781458HCID 87781458, compound

Product 1

HCID 69328059HCID 69328059, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,5-dichloro-N-trifluoroacetyl-O-[(6-methoxy)-2-naphthyl]-L-tyrosine methyl ester (160 mg, 0.31 mmol), 47% hydrobromic acid (3 ml) and acetic acid (2 ml) was heated under reflux for 5 hrs. The reaction mixture was diluted with water (10 ml), adjusted to pH 4-5 with 4N sodium hydroxide under ice cooling and then stirred at room temperature for 30 min. The precipitates were collected by filtration, washed with water and dried under reduced pressure to give 3,5-dichloro-O-[(6-hydoxy)-2-naphthyl]-L-tyrosine (92 mg, 76%) as a pale orange powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hrs
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-5bd26263933d485e9adf1a3e925e8a2d
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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