2-[(Acetylthio)methyl]-3-phenylpropionic Acid → N-(3-Acetylthio-2-benzylpropionyl)-O-benzyl-L-tyrosine Methyl Ester

HRID 1651722Notes

Reaction equation

HRID 1651722 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:22])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[NH2:6].[C:23]([S:26][CH2:27][CH:28]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:29](O)=[O:30])(=[O:25])[CH3:24]>CO>[CH3:2][O:3][C:4](=[O:22])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][CH:9]=1)[NH:6][C:29](=[O:30])[CH:28]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:27][S:26][C:23](=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 12616037H-Tyr(Bzl)-OMe.HCl

Product 1

HCID 14390719N-(3-Acetylthio-2-benzylpropionyl)-O-benzyl-L-tyrosine Methyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

React O-benzyl-L-tyrosine methyl ester hydrochloride (2.77 g) and 3-acetylthio-2-benzylpropionic acid (2.05 g) in a manner similar to that described in Example 1, Step 1 to give a yellow-orange oil. Chromatograph this oil on a column of silica gel (2.5L) and elute with CH2Cl2 : ethyl acetate 98:2 to give Isomer A, a white solid (0.84 g) m.p. 108°-109°; [α]D26 =-39.8° (MeOH); overlap Isomer A and Isomer B (0.80 g); and Isomer B, white solid (0.45 g), m.p. 92°-93°, [α]D26 =+19.2° (MeOH).

Workup

  1. customto give a yellow-orange oil
  2. washChromatograph this oil on a column of silica gel (2.5L) and elute with CH2Cl2 : ethyl acetate 98:2
  3. customto give Isomer A

Sources & evidence

ORD record
ord-1a89140ddba74641a8253e5f7bc76e56
Source dataset
uspto-grants-1990_05
Patent number
US04929641

Reaction notes

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