(S)-(-)-N-Benzyl-1-phenylethylamine → (S)-3-[2-(4-Acetylaminophenyl)ethyl]-3-hydroxy-4-methylpentanoic Acid (S)-N-Benzyl-alpha-methylbenzylamine Salt

HRID 844830

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:21])([CH:18]([CH3:20])[CH3:19])[CH2:14][C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:22]([NH:29][C@@H:30]([CH3:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[CH2:22]([NH:29][C@@H:30]([CH3:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][C@@:13]([OH:21])([CH:18]([CH3:19])[CH3:20])[CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

Ethanol (125 g) was added to (+/−)-3-[2-(4-acetylaminophenyl)ethyl]-3-hydroxy-4-methylpentanoic acid (11a, 25 g, 85 mmol) and the resulting solution stirred at 20° C. (S)-N-Benzyl-α-methylbenzylamine (21, 22.5 g, 106 mmol) was added to the solution and the resulting mixture allowed to stir at 20° C. for 23 hours. The mixture was filtered and the product washed with ethanol (10 mL) and vacuum dried at ambient temperature to give (S)-3-[2-(4-acetylaminophenyl)ethyl]-3-hydroxy-4-methylpentanoic acid (S)-N-benzyl-α-methylbenzylamine salt (22a): 18.6 g (36.8 mmol, 43% yield or 86% of theory); Chiral assay (HPLC): 99.2 area % (S) isomer 23a; mp: 152-154° C.

Workup

additionwas added to the solution
filtrationThe mixture was filtered
washthe product washed with ethanol (10 mL) and vacuum
customdried at ambient temperature

Sources & evidence

ORD record: ord-a06b05bdbbdc43fe9632c2941295f96a
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380400B1

Linked notes

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