D-Tyrosine → HCID 67676288, compound

HRID 1957023Notes

Reaction equation

HRID 1957023 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[N:5]([C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)[CH3:6].N[C@@H](C(O)=O)C[C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:20][CH:19]=1)[N:5]([C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)[CH3:6]

Participants

4

Reactant 2

HCID 71098D-TyrosineHCID 67674941HCID 67674941, compound

Product 1

HCID 67676288HCID 67676288, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3,5-dimethylbenzoyl)-N-methyl-(D)-tyrosine methyl ester (253 mg, 0.74 mmol) (prepared from (D)-tyrosine following the procedure described in example 55), Ph3Bi(OAc)2 [triphenylbismuth diacetate] (895 mg, 1.6 mmol) (prepared according to the literature procedure; H. Brunner, U. Obermann, and P. Winner, Organometallics 1989, 8, 821-826), and Cu powder (43 mg, 0.68 mmol) in methylene chloride (15 ml) is stirred at room temperature under nitrogen atmosphere overnight. This reaction mixture is concentrated in vacuo and the crude material is chromatographed on silica with hexane/ethylacetate (3:1) to give N-(3,5-dimethylbenzoyl)-N-methyl-O-phenyl-(D)-tyrosine methyl ester as a colorless oil. Hydrolysis of the methyl ester obtained above (294 mg, 0.70 mol) by lithium hydroxide hydrate (31 mg, 0.74 mol) gives a corresponding acid.

Workup

  1. customprepared
  2. concentrationThis reaction mixture is concentrated in vacuo
  3. customthe crude material is chromatographed on silica with hexane/ethylacetate (3:1)

Sources & evidence

ORD record
ord-4ec85ad94c1b43028fa4a218b6ca67de
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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