2-[(Acetylthio)methyl]-3-phenylpropionic Acid → HCID 14390715, compound

HRID 346183Notes

Reaction equation

HRID 346183 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C@H:5]([CH2:7][CH2:8][S:9][CH2:10][CH3:11])[NH2:6])[CH3:2].[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>[CH2:1]([O:3][C:4](=[O:12])[C@H:5]([CH2:7][CH2:8][S:9][CH2:10][CH3:11])[NH:6][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])[CH3:2]

Participants

4

Reactant 2

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 14770805HCID 14770805, compound

Product 1

HCID 14390715HCID 14390715, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

React L-ethionine ethyl ester (3.51 g) and 3-acetylthio-2-benzylpropionic acid (4.37 g) in a manner similar to that described in Example 1, Step 1 to give a yellow residue. Chromatograph the yellow residue on the Waters Prep 500 (2 silica gel cartridges) and elute with ethyl acetate:hexane 2:18 (16 L), then ethyl acetate:hexane 3:17. Repeat chromatography of the fractions using ethyl acetate:hexane as eluant to give Isomer A, a white solid (0.89 g), m.p. 84°-90°, [α]D26 =-60.6° (MeOH) and Isomer B (0.82 g), m.p. 79°-84°, [α]D26 =-0.3° (MeOH).

Workup

  1. customto give a yellow residue
  2. washelute with ethyl acetate:hexane 2:18 (16 L)
  3. customhexane as eluant to give Isomer A

Sources & evidence

ORD record
ord-f7b8a5a2cd8145b6a7bef5b5a237c0c5
Source dataset
uspto-grants-1991_10
Patent number
US05061710

Reaction notes

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