Diisopropylcarbodiimide → 3-(4,5-Dimethoxy-2-nitro benzyloxycarbonyl-amino)-butyric acid 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester

HRID 12013

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[C:33]([O:34][CH3:35])=[CH:32][C:20]([CH2:21][O:22][C:23]([NH:25][CH:26]([CH3:31])[CH2:27][C:28](O)=[O:29])=[O:24])=[C:19]([N+:36]([O-:38])=[O:37])[CH:18]=1.CC(C)N=C=NC(C)C>C1COCC1>[O:13]=[C:12]1[CH:11]=[CH:10][C:9](=[O:14])[N:8]1[C:5]1[CH:4]=[CH:3][C:2]([O:1][C:28](=[O:29])[CH2:27][CH:26]([NH:25][C:23]([O:22][CH2:21][C:20]2[CH:32]=[C:33]([O:34][CH3:35])[C:17]([O:16][CH3:15])=[CH:18][C:19]=2[N+:36]([O-:38])=[O:37])=[O:24])[CH3:31])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(4-Hydroxy-phenyl)-pyrrole-2,5-dione (1 mmol), NHS (1.0 mmol) and 3-(4,5-dimethoxy-2-nitro-benzyloxycarbonylamino)-butyric acid (1 mmol) is dissolved in THF (3 mL). The solution is cooled to 0° C. and treated dropwise with DIC (1.2 mmol). The cooling bath is removed after 1 hour and the reaction mixture is left at room temperature o/n. The solvent is evaporated in vacuo and the pure product (3-(4,5-dimethoxy-2-nitro benzyloxycarbonyl-amino)-butyric acid 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-phenyl ester) is isolated by silica column purification using EtOAc-heptane (1:4 then 1:2 then 1:1) as eluent.

Workup

customThe cooling bath is removed after 1 hour
waitthe reaction mixture is left at room temperature o/n
customThe solvent is evaporated in vacuo

Sources & evidence

ORD record: ord-ef4d96badb8b48f0bcb90ff68efff15e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727713B2

Linked notes

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