Pyridine → HCID 13014004, compound

HRID 1733419Notes

Reaction equation

HRID 1733419 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[C:8]([N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])(OCC)=O.[CH2:24](N(CC)CC)C.N[C@H:32]([C:41]([OH:43])=[O:42])CC1C=CC(O)=CC=1.N1[CH:49]=[CH:48][CH:47]=[CH:46]C=1>CS(C)=O.O>[C:5]([O:4][C:1]1[CH:49]=[CH:48][C:47]([CH2:46][CH:8]([N:13]2[C:14](=[O:23])[C:15]3=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]3[C:17]2=[O:18])[CH2:32][C:41]([OH:43])=[O:42])=[CH:24][CH:2]=1)(=[O:7])[CH3:6]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6057L-Tyrosine2×HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 13014004HCID 13014004, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

O-Acetyl-N-phthaloyltyrosine (m.p. 176°-179° C., prepared in 81% yield by treating N-phthaloyltyrosine with acetic anhydride in pyridine; the N-phthaloyltyrosine being prepared in 91% yield from N-carbethoxyphthalimide, triethylamine and L-tyrosine in dimethyl sulphoxide in view of the poor solubility of L-tyrosine in water) is treated substantially by the procedure described in Example 1 (1) to give 4-(4-acetoxyphenyl)-3-phthalimidobutanoic acid in 49% yield, m.p. 151°-153.5° C.

Workup

  1. additionis treated substantially by the procedure

Sources & evidence

ORD record
ord-0dcea4aae1934f12a5b0ea0861c57a3d
Source dataset
uspto-grants-1980_12
Patent number
US04242256

Reaction notes

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