Ethylene Glycol → Bupivacaine (USAN:INN:BAN)

HRID 1934816Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.C(O)CO>O>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:10]([C:11]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:21])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

Conditions

Temperature: 138 °C

Procedure

A mixture of (S)-bupivacaine (>99% ee, 1.5 g mmol), ethylene glycol (13.5 ml) and water (1.5 ml) was heated at 138° C. for 9 hours. On cooling to ambient temperature crystallisation of a solid occurred. The solid was filtered to give a quantitative yield of bupivacaine which was shown by chiral HPLC analysis to be a 52:48 mixture of (S)-bupivacaine and (R)-bupivacaine.

Workup

temperatureOn cooling to ambient temperature
customcrystallisation of a solid
filtrationThe solid was filtered

Sources & evidence

ORD record: ord-c195efdbbea9432992f63b9894e48705
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384227B2

Reaction notes

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