Dimethylformamide → HCID 66661058, compound

HRID 472794Notes

Reaction equation

Br[CH2:2][CH2:3][OH:4].[CH2:5]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=1)[O:25][CH2:26][C:27]([OH:29])=[O:28])=[O:20])=[CH:14][CH:13]=[CH:12]2)[CH2:6][CH2:7][CH3:8].C([O-])(O)=O.[Na+].CN(C=O)C>CCOC(C)=O.O>[CH2:5]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=1)[O:25][CH2:26][C:27]([O:29][CH2:2][CH2:3][OH:4])=[O:28])=[O:20])=[CH:14][CH:13]=[CH:12]2)[CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: 70 °C

Procedure

2-Bromoethanol was added to a 1 dram vial containing a mixture of 2-(3-(6-butyl-1-naphthamido)phenoxy)acetic acid (27 mg, 0.07 mmol), NaHCO3 (6 mg, 0.07 mmol) and DMF (03 mL). A single drop of water from a 22 gauge needle was added and the vial was sealed under nitrogen and heated at 70° C. After several days, the mixture was cooled to room temperature and diluted with EtOAc (20 The organic mixture was and washed with water (2×5 mL) and brine (5 mL) then dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified on 4 g silica gel (100% hexanes→100% EtOAc, gradient) to afford 24 mg (69%) of the title compound.

Workup

additioncontaining
customthe vial was sealed under nitrogen
waitAfter several days
temperaturethe mixture was cooled to room temperature
washwashed with water (2×5 mL) and brine (5 mL)
dry with materialthen dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified on 4 g silica gel (100% hexanes→100% EtOAc, gradient)

Sources & evidence

ORD record: ord-0c63198115104ee7a3aa460e0b5de61f
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633220B2

Reaction notes

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