2-Methoxyethanol → HCID 22276584, compound

HRID 1063905Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][S:9]([O:12][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][CH2:22][CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]([S:9]([O:12][N:13]1[C:14](=[O:19])[CH2:15][CH2:16][C:17]1=[O:18])(=[O:10])=[O:11])[CH2:23][CH2:22][O:21][CH3:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(t-butoxycarbonylaminosulfonyloxy)-succinimide (272 mg), 2-methoxyethanol (84.4 mg) and triphenylphosphine (291 mg) in tetrahydrofuran (5 ml) was added diethyl azodicarboxylate (193 mg) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. After evaporation of solvent, the residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (2:1, 1:1) to give N-(N-t-butoxycarbonyl-N-(2-methoxyethyl)aminosulfonyloxy)succinimide as colorless oil (205 mg).

Workup

customAfter evaporation of solvent
customthe residue was purified by silica gel column chromatography
washeluting with a mixture of hexane and ethyl acetate (2:1, 1:1)

Sources & evidence

ORD record: ord-c30d2af808274ff892df3c9af68590c8
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06967197B2

Reaction notes

Loading…