Allyl Alcohol → Allyl 2-(methyl(4-(methylsulfonamido)benzyl)amino)acetate

HRID 1776506Notes

Reaction equation

Cl.[CH3:2][N:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[CH2:4][C:5]([OH:7])=[O:6].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:32](O)[CH:33]=[CH2:34]>CC#N.CCOC(C)=O>[CH3:2][N:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[CH2:4][C:5]([O:7][CH2:34][CH:33]=[CH2:32])=[O:6]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-(methyl(4-(methylsulfonamido)benzyl)amino)acetic acid hydrochloride (1.054 g, 3.41 mmol), CDI (1.107 g, 6.83 mmol), and TEA (0.952 ml, 6.83 mmol) in CH3CN (80 ml) was heated at 75° C. for 3 hours. The solvent was evaporated; the residue was dissolved in prop-2-en-1-ol (30 ml, 439 mmol) and heated at 75° C. for 1 hour. The mixture was diluted with EtOAc and washed several times with NH4Cl sat. sol. The organic phase was dried over Na2SO4, the solvent was removed, and the residue was filtered on SCX cartridge (DCM/MeOH 1/1; conc.aq.NH4OH/MeOH 1/9). The basic fraction was evaporated to dryness to give allyl 2-(methyl(4-(methylsulfonamido)benzyl)-amino)acetate as a brown oil (0.942 g, 3.02 mmol, 88% yield, MS/ESI+ 313.2 [MH]+).

Workup

customThe solvent was evaporated
temperatureheated at 75° C. for 1 hour
washwashed several times with NH4Cl sat. sol. The organic phase
dry with materialwas dried over Na2SO4
customthe solvent was removed
filtrationthe residue was filtered on SCX cartridge (DCM/MeOH 1/1; conc.aq.NH4OH/MeOH 1/9)
customThe basic fraction was evaporated to dryness

Sources & evidence

ORD record: ord-f503b6d95e6b42899920f547adecedf7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265768B2

Reaction notes

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