Acetate → 3,5-dichloro-N-trifluoroacetyl-O-(1-naphthyl)-L-tyrosine methyl ester

HRID 1393374Notes

Reaction equation

HRID 1393374 reaction equation
N1C=CC=CC=1.C(N(CC)CC)C.[CH3:14][O:15][C:16](=[O:35])[C@H:17]([CH2:25][C:26]1[CH:31]=[C:30]([Cl:32])[C:29]([OH:33])=[C:28]([Cl:34])[CH:27]=1)[NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21].[C:36]1(B(O)O)[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1.C([O-])(=O)C>ClCCCl.C(OCC)(=O)C>[CH3:14][O:15][C:16](=[O:35])[C@H:17]([CH2:25][C:26]1[CH:27]=[C:28]([Cl:34])[C:29]([O:33][C:44]2[C:45]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:41]=[CH:42][CH:43]=2)=[C:30]([Cl:32])[CH:31]=1)[NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22]

Participants

8

Reactant 5

HCID 175AcetateHCID 1049PyridineHCID 8471TriethylamineHCID 2545321-Naphthaleneboronic acidHCID 150239503,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester

Product 1

HCID 865983193,5-dichloro-N-trifluoroacetyl-O-(1-naphthyl)-L-tyrosine methyl esterYield 22.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine (0.584 ml, 7.22 mmol) and triethylamine (0.968 ml, 6.94 mmol)were added in turn to a suspension of 3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester (500 mg, 1.39 mmol), 1-naphthlene boronic acid (765 mg, 4.44 mmol), molecular sieves 4A powder (720 mg) and cppoer(II) acetate (390 mg, 2.08 mmol) in 1,2-dichloroethane(20 ml), and the mixture was stirred under air atmosphere (without argon) at room temperature for 24 hrs. The reaction mixture was diluted with ethyl acetate, and the insoluble materials were filtered off (celite (Trade mark)) and washed with ethyl acetate. The filtrate and washings were combined, washed with 10% hydrochloric acid and brine in turn and dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/diethyl ether=2) to give 3,5-dichloro-N-trifluoroacetyl-O-(1-naphthyl)-L-tyrosine methyl ester (151 mg, 22%) as colorless crystals.

Workup

  1. filtrationthe insoluble materials were filtered off (celite (Trade mark))
  2. washwashed with ethyl acetate
  3. washwashed with 10% hydrochloric acid and brine in turn
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (n-hexane/diethyl ether=2)

Sources & evidence

ORD record
ord-8d87f243954e486b8e13bd92157a35e4
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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