2-[(Acetylthio)methyl]-3-phenylpropionic Acid → HCID 14770728, compound

HRID 257535Notes

Reaction equation

HRID 257535 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:18])[C@H:5]([CH2:7][S:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[NH2:6].[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>[CH3:2][O:3][C:4](=[O:18])[C@H:5]([CH2:7][S:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[NH:6][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]

Participants

4

Reactant 2

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 14390799HCID 14390799, compound

Product 1

HCID 14770728HCID 14770728, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

React S-(4-methoxybenzyl)-L-cysteine methyl ester hydrochloride (1.85 g) and 3-acetylthio-2-benzylpropionic acid (1.95 g) in the manner described in Example 1, Step 1 to give an amber oil. Chromatograph this oil on a column of silica gel (2L, 60-200 mesh) and elute with ethyl acetate:hexane 5:20 to give Isomer A, a clear oil (0.63 g), [α]D26 =-66.5° (MeOH), overlap Isomer A and Isomer B (0.28 g); and Isomer B, a clear oil (0.67 g), [α]D26 =+3.0° (MeOH).

Workup

  1. customto give an amber oil
  2. washChromatograph this oil on a column of silica gel (2L, 60-200 mesh) and elute with ethyl acetate:hexane 5:20
  3. customto give Isomer A

Sources & evidence

ORD record
ord-2a9f412870de47fdb58119155840c8bc
Source dataset
uspto-grants-1993_11
Patent number
US05262436

Reaction notes

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