Succinic anhydride → 3-[3-(3-Tert-butyloxycarbonylaminophenyl)-1,2,4-oxadiazol-5-yl]propionic acid

HRID 584122Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

Succinic anhydride (14 mg, 0.14 mmol) and [3-(N-hydroxycarbamimidoyl)-phenyl]-carbamic acid tert-butyl ester (35 mg, 0.14 mmol) were dissolved in 0.25 mL DMF and heated at 120° C. for 2 h. The cooled solution was evaporated and dried to yield 3-[3-(3-tert-butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-5-yl]-propionic acid which was used without further purification.

Workup

customThe cooled solution was evaporated
customdried

Sources & evidence

ORD record: ord-45f2726504e34f3b8de66244cb47619b
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924284B2

Reaction notes

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