2-[(Acetylthio)methyl]-3-phenylpropionic Acid → HCID 14770732, compound

HRID 257536Notes

Reaction equation

HRID 257536 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([CH3:18])[CH:12]=1)[NH2:7])[CH3:3].[C:20]([S:23][CH2:24][CH:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:26](O)=[O:27])(=[O:22])[CH3:21]>CO>[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([CH3:18])[CH:12]=1)[NH:7][C:26](=[O:27])[CH:25]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:24][S:23][C:20](=[O:22])[CH3:21])[CH3:3]

Participants

4

Reactant 2

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 14390803HCID 14390803, compound

Product 1

HCID 14770732HCID 14770732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

React S-(3,4-dimethylbenzyl)-L-cysteine ethyl ester hydrochloride (2.20 g) and 3-acetylthio-2-benzylpropionic acid (1.74 g) in the manner described in Example 1, Step 1 to give an amber oil. Place the oil on a column of silica gel (1L) and elute with ethyl acetate:hexane 25:170 (4L) and then methanol:hexane 25:170 to give a light orange oily solid. Repeat the chromatography to give Isomer A, a white solid (0.52 g), m.p. 89.5°-92.5°, [α]D26 =-71.1° (MeOH) and Isomer B, a white solid (0.60 g), m.p. 51°-55°, [α]D26 =-8.4° (MeOH).

Workup

  1. customto give an amber oil
  2. washelute with ethyl acetate:hexane 25:170 (4L)
  3. custommethanol:hexane 25:170 to give a light orange oily solid
  4. customRepeat the chromatography to give Isomer A

Sources & evidence

ORD record
ord-e9b521b644c242b886b925a42f60cbd0
Source dataset
uspto-grants-1993_11
Patent number
US05262436

Reaction notes

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