Succinic anhydride → N-[4-(tert-Butoxycarbonylamino-methyl)-benzyl]-succinamic acid

HRID 1827340Notes

Reaction equation

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

Participants

Conditions

Temperature: 36 °C

Procedure

A mixture of the above compound (27) (2.0 g, 8.5 mmol) and succinic anhydride (0.85 g, 8.5 mmol) in DCM (50 mL) were stirred at 36° C. for several hours. The product was diluted with 5% citric acid and extracted with DCM (3×50 mL). The combined extracts were washed with brine and dried over MgSO4 to give 2.1 g (28) (72%) of the desired compound. MS (ESI−) m/z 335.23 (M−H+).

Workup

extractionextracted with DCM (3×50 mL)
washThe combined extracts were washed with brine
dry with materialdried over MgSO4

Sources & evidence

ORD record: ord-dafbe11057fe43959eaf471e84764d34
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053214B2

Reaction notes

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