2-[(Acetylthio)methyl]-3-phenylpropionic Acid → HCID 14390700, compound

HRID 346182Notes

Reaction equation

HRID 346182 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][S:7][C:8]([CH3:11])([CH3:10])[CH3:9])[NH2:5].[C:13]([S:16][CH2:17][CH:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19](O)=[O:20])(=[O:15])[CH3:14]>CO>[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][S:7][C:8]([CH3:9])([CH3:11])[CH3:10])[NH:5][C:19](=[O:20])[CH:18]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:17][S:16][C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 11819880HCID 11819880, compound

Product 1

HCID 14390700HCID 14390700, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

React S-(t-butyl)-L-cysteine methyl ester (2.32 g) and 3-acetylthio-2-benzylpropionic acid (3.22 g) in the manner described in Example 1, Step 1 to give an orange solid. Chromatograph this solid on a column of silica gel (2 L, 60-200 mesh) and elute with ethyl acetate:hexane 3:17 to give Isomer A, a clear oil (1.09 g), [α]26 =-44.9° (MeOH); overlap Isomer A and Isomer B (0.52 g); and Isomer B, a clear oil (0.75 g), [α]D26 =+8.3° (MeOH).

Workup

  1. customto give an orange solid
  2. washChromatograph this solid on a column of silica gel (2 L, 60-200 mesh) and elute with ethyl acetate:hexane 3:17
  3. customto give Isomer A

Sources & evidence

ORD record
ord-3bb27b46ac4a41b8b04095393e3a9825
Source dataset
uspto-grants-1991_10
Patent number
US05061710

Reaction notes

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