HCID 67139799, compound → HCID 67138409, compound

HRID 1592033Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:35])[C:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:19]=1)([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])C(OC)=O>CS(C)=O.O>[CH3:1][O:2][C:3](=[O:35])[CH:4]([NH:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:19]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of the title E compound, 2-(3-benzyloxy-4-nitro-benzyl)-2-t-butoxycarbonylamino-malonic acid dimethyl ester (6.98 g, 14.3 mmol) in DMSO (68 mL) and water (1.46 mL) sodium chloride (0.85 g, 14.6 mmol) is added and the mixture is gradually heated to 150° C. for 1 h. The mixture is cooled to RT, diluted with water (300 mL) and extracted 3 times with EtOAc. The organic extracts are washed with water and brine, dried over anhydrous MgSO4, decolorized with charcoal, filtered and evaporated. The residue is purified by chromatography (silica gel column, 6×30 cm, on EtOAc-hexane 1:1) to give 3-(3-Benzyloxy-4-nitro-phenyl)-2-tert-butyloxycarbonylamino-propionic acid methyl ester as a crystalline solid: mp=104-105° C.

Workup

temperatureThe mixture is cooled to RT
extractionextracted 3 times with EtOAc
washThe organic extracts are washed with water and brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customevaporated
customThe residue is purified by chromatography (silica gel column, 6×30 cm, on EtOAc-hexane 1:1)

Sources & evidence

ORD record: ord-89e0746d869c4fec9ce9df1b38d8a28a
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291635B2

Reaction notes

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