Potassium Carbonate → HCID 54241176, compound

HRID 1609015Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:21][CH:22]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 79177tert-Butyl bromoacetate

HCID 11508180Z-D-Tyrosine methyl ester

Product 1

HCID 54241176HCID 54241176, compound

Procedure

(R)-N-benzyloxycarbonyl-tyrosine methyl ester was reacted in a manner analogous to that described in Example 3 with t-butyl bromoacetate in the presence of potassium carbonate to give N-benzyloxycarbonyl-3-[p-(tert-butoxycarbonylmethoxy)phenyl]-D-alanine methyl ester. The colorless oil was hydrogenated in methanol, after addition of 5% palladium/carbon, in a shaking apparatus at room temperature under atmospheric pressure, obtaining, after filtration and removal of the solvent, 3-[p-(tert-butoxycarbonylmethoxy)phenyl]-D-alanine methyl ester in the form of a colorless oil.

Sources & evidence

ORD record: ord-e778e2fed30b47cb92a5e85fb7606e3b
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05399585

Reaction notes

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