2-[(Acetylthio)methyl]-3-phenylpropionic Acid → HCID 14390696, compound

HRID 257537Notes

Reaction equation

HRID 257537 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:18])[C@H:6]([CH2:8][S:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:7])[CH3:3].[C:19]([S:22][CH2:23][CH:24]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:25](O)=[O:26])(=[O:21])[CH3:20]>CO>[CH2:2]([O:4][C:5](=[O:18])[C@H:6]([CH2:8][S:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:7][C:25](=[O:26])[CH:24]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:23][S:22][C:19](=[O:21])[CH3:20])[CH3:3]

Participants

4

Reactant 2

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 13500736HCID 13500736, compound

Product 1

HCID 14390696HCID 14390696, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

React S-phenethyl-L-cysteine ethyl ester hydrochloride (2.85 g) and 3-acetylthio-2-benzylpropionic acid, (2.38 g) in a manner similar to that described in Example 1, Step 1 to give an amber oil. Chromatograph this oil on Prep 500 (2 silica gel cartridges) and elute with CH2Cl2 (4L) and then CH2Cl2 :ethyl acetate 100:2 to give Isomer A, a white solid (1.32 g), m.p. 63°-64°[α]D26 =-51.2° (MeOH); overlap Isomer A and Isomer B (0.63 g); and Isomer B, white solid (1.14 g), m.p. 84°-86°, [α]D26 =+5.3° (MeOH).

Workup

  1. customto give an amber oil
  2. washChromatograph this oil on Prep 500 (2 silica gel cartridges) and elute with CH2Cl2 (4L)
  3. customCH2Cl2 :ethyl acetate 100:2 to give Isomer A

Sources & evidence

ORD record
ord-ca131f0645c84bb99eb7fa76f7608587
Source dataset
uspto-grants-1993_11
Patent number
US05262436

Reaction notes

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