Itaconic acid → STK087815

HRID 859202Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([OH:24])(=[O:23])[C:17]([CH2:19][C:20](O)=[O:21])=[CH2:18]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:13]2[C:20](=[O:21])[CH2:19][CH:17]([C:16]([OH:24])=[O:23])[CH2:18]2)=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 811Itaconic acid

HCID 228604-Benzyloxyaniline

Product 1

HCID 2968114STK087815Yield 96.2%

Conditions

Temperature: 130 °C

Procedure

18.8 g (94.4 mmol) of 4-benzyloxyaniline are mixed with 12.28 g (94.4 mmol) itaconic acid. The solid mixture is heated to 130° C. After 20 min the molten material solidifies. After cooling, the resulting solid is triturated with ethyl acetate to yield 28.26 g (96% of theory) of (RS)-1-(4-benzyloxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid as a greyish solid. MS: m/e=311 (M)+.

Workup

temperatureAfter cooling
customthe resulting solid is triturated with ethyl acetate

Sources & evidence

ORD record: ord-d2c1f1d1ab794804bd1e99d02e1040b9
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151111B2

Reaction notes

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