2-Ethylhexanoic Acid → N-[(S)-alpha-methylbenzyl]-(S)-proline

HRID 565723Notes

Reaction equation

C[O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C@@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(C(CCCC)C(O)=O)C>O>[CH3:16][C@H:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:3]([OH:17])=[O:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To N-[(S)-α-methylbenzyl]-(S)-proline methyl ester (4.46 g) obtained in Example 3 were added water (9.33 g) and 2-ethylhexanoic acid (3.25 g). The mixture was heated up to 60° C. and stirred at that temperature for 12 hours. The resulting mixture was washed with heptane to yield an aqueous N-[(S)-α-methylbenzyl]-(S)-proline solution.

Workup

washThe resulting mixture was washed with heptane

Sources & evidence

ORD record: ord-de20c2ac2eb74766a034cf14e5003d3c
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172234B2

Reaction notes

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