Methyl N-(triethylammoniosulfonyl)carbamate → tert-butyl 4-[(4S)-4-(methoxycarbonyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-indole-1-carboxylate

HRID 2389371Notes

Reaction equation

[OH:1][CH2:2][C@H:3]([NH:8][C:9]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=O)[C:4]([O:6][CH3:7])=[O:5].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CCOC(C)=O>[CH3:7][O:6][C:4]([C@@H:3]1[CH2:2][O:1][C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])=[N:8]1)=[O:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate (2.09 g) in THF (21.0 mL) was added Burgess Reagent (1.44 g) at ambient temperature and the mixture was stirred at 70° C. for 45 minutes. The resulting mixture was diluted with EtOAc (60 mL) and washed successively with saturated NaHCO3 aqueous solution and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=2:1) to afford tert-butyl 4-[(4S)-4-(methoxycarbonyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-indole-1-carboxylate (1.35 g) as a colorless amorphous.

Workup

washwashed successively with saturated NaHCO3 aqueous solution and brine
dry with materialThe organic layer was dried over anhydrous MgSO4
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=2:1)

Sources & evidence

ORD record: ord-541ba14ba56642a286980a8b836473dd
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273745B2

Reaction notes

Loading…