L-Pyroglutamic Acid → tetrabutylphosphonium (S)-(-)-2-pyrrolidone-5-carboxylate

HRID 1474582Notes

Reaction equation

HRID 1474582 reaction equation
[NH:1]1[C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][C:2]1=[O:9].[OH-].[CH2:11]([P+:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>>[NH:1]1[C@H:5]([C:6]([O-:8])=[O:7])[CH2:4][CH2:3][C:2]1=[O:9].[CH2:24]([P+:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:25][CH2:26][CH3:27]

Participants

3

Reactant 2

HCID 7405L-Pyroglutamic AcidHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Product 1

HCID 86626712tetrabutylphosphonium (S)-(-)-2-pyrrolidone-5-carboxylateYield 105.5%

Procedure

At 0° C., 4.2 g of (S)-(−)-2-pyrrolidone-5-carboxylic acid (by Wako Pure Chemical Industry) was added to 21.3 g of tetrabutylphosphonium hydroxide (aqueous 41.4% solution, by Hokko Chemical), and stirred for 10 minutes. Using an evaporator, the pressure was reduced to 40 to 50 mmHg, and this was concentrated at 60 to 80° C. for 2 hours, and then at 90° C. for 3 hours. Thus, 13.3 g of tetrabutylphosphonium (S)-(−)-2-pyrrolidone-5-carboxylate (purity: 94.1%) was obtained as an oily compound. The obtained ionic liquid had the same properties as in Production Example 1.

Workup

  1. customan evaporator
  2. concentrationthis was concentrated at 60 to 80° C. for 2 hours
  3. waitat 90° C. for 3 hours

Sources & evidence

ORD record
ord-ca6fa63665f8497bb6791eb286a5f0c7
Source dataset
uspto-grants-2015_04
Patent number
US09018321B2

Reaction notes

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