Acetone → 5-(2,5-Dioxo-1-pyrrolidinyl) hydrogen N-(15-carboxy-1-oxopentadecyl)-L-glutamate

HRID 1632007Notes

Reaction equation

O=C1CCC(=O)N1[O:8][C:9](=[O:50])[C@@H:10]([NH:23][C:24](=[O:49])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41]CC1C=CC=CC=1)=[O:40])[CH2:11]CC(OCC1C=CC=CC=1)=O.F[C:52](F)(F)[C:53]([OH:55])=[O:54].[H][H].C[C:61]([CH3:63])=[O:62]>[Pd]>[O:49]=[C:24]1[CH2:25][CH2:63][C:61](=[O:62])[N:23]1[O:55][C:53](=[O:54])[CH2:52][CH2:11][C@H:10]([NH:23][C:24](=[O:49])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])[C:9]([OH:50])=[O:8]

Participants

Conditions

Temperature: 20 °C

Procedure

(S)-2-(15-benzyloxycarbonyl-pentadecanoylamino)-pentanedioic acid 5-benzyl ester 1-(2,5-dioxo-pyrrolidin-1-yl) ester (5.0 g, 7.3 mmol) was dissolved in acetone (95 ml) containing trifluoroacetic acid (95 μl). Palladium on carbon, 10% (0.50 g) was added. Under stirring at 30-35° C. hydrogen was added. When the consumption of hydrogen stopped the reaction mixture was filtered. The filtrate was cooled to 20° C. and n-heptane (140 ml) was added over a period of 15-30 minutes. The resulting suspension was cooled to 0-5° C. for 2-3 hours. The product was isolated by filtration, and dried to constant weight under reduced pressure at 20-25° C. Yield 3 g (84%) of white material.

Workup

additionwas added
customWhen the consumption of hydrogen
filtrationwas filtered
additionn-heptane (140 ml) was added over a period of 15-30 minutes
temperatureThe resulting suspension was cooled to 0-5° C. for 2-3 hours
customThe product was isolated by filtration
customdried to constant weight under reduced pressure at 20-25° C

Sources & evidence

ORD record: ord-f6cfab9f82e341089b509fe27c0bb26f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791236B2

Reaction notes

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