Diisopropylethylamine → HCID 121289145, compound

HRID 1484209Notes

Reaction equation

[CH:1]1([O:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=2)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.[CH2:35]1[C:40](=[O:41])[N:39]([O:42][C:43](ON2C(=O)CCC2=O)=[O:44])[C:37](=[O:38])[CH2:36]1>C(#N)C>[CH:1]1([O:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([O:25][C:43]([O:42][N:39]3[C:40](=[O:41])[CH2:35][CH2:36][C:37]3=[O:38])=[O:44])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=2)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

Conditions

Temperature: 30 °C

Procedure

The product 36 obtained above (80 mg, 0.23 mmol) was dissolved in 4.1 g acetonitrile. Diisopropylethylamine (215 mg, 1.67 mmol) was added, followed by N,N′-disuccinimidyl carbonate (217 mg, 0.85 mmol). The solution was stirred for 2 days at ca. 30° C. The solvent was removed by rotary evaporation and the residue was chromatographed on 16 g silica, using dichloromethane with gradually increasing amounts of TBME as the eluent. The product eluted with ca. 20% TBME. Rotary evaporation of the product fractions afforded the product minor-(E)-ethyl 2-(4-(((cyclooct-2-en-1-yloxy)carbonyl)amino)phenyl)-2-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)acetate (37) as a viscous oil (60 mg, 0.123 mmol, 53%).

Workup

customThe solvent was removed by rotary evaporation
customthe residue was chromatographed on 16 g silica
washThe product eluted with ca. 20% TBME
customRotary evaporation of the product fractions

Sources & evidence

ORD record: ord-fe08490a541b44d6998d685a96b22af6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421274B2

Reaction notes

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