Phthalic Anhydride → HCID 67481558, compound

HRID 1400656Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:6]([OH:8])=[O:7].[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12>CN(C=O)C>[C:13]([O:12][C:10]([NH:9][C@@H:5]([CH2:4][CH2:3][CH2:2][N:1]1[C:20](=[O:21])[C:19]2[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]1=[O:22])[C:6]([OH:8])=[O:7])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (S)-5-amino-2-(tert-butoxycarbonylamino)pentanoic acid XLIX (6.64 g, 28.6 mmol) in DMF (150 mL) was added phthalic anhydride (4.3 g, 29.0 mmol). The mixture was placed in a tightly closed ampule and heated at 120° C. for 24 h. After the reaction was complete, the solvent was evaporated under vacuum and the residue was subjected to column chromatography on silica gel (100:1 DCM:MeOH→10:1 DCM:MeOH) affording (S)-2-(tert-butoxycarbonylamino)-5-(1,3-dioxoisoindolin-2-yl)pentanoic acid L (8.92 g, 24.6 mmol, 86%). ESIMS found for C18H22N2O6 m/z 361 (M−H)−.

Workup

customthe solvent was evaporated under vacuum

Sources & evidence

ORD record: ord-42b3b724e72f451caab313b0ff9252cc
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906868B2

Reaction notes

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