Hydrogen Bromide → methyl 2-((S)-1-amino-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate hydrobromide

HRID 494377Notes

Reaction equation

HRID 494377 reaction equation
Br.C(OC([NH:12][C@H:13]([C:17]1[O:18][C:19]([C:26]2[C:34]3[C:29](=[C:30]([Br:35])[CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)=[C:20]([C:22]([O:24][CH3:25])=[O:23])[N:21]=1)[CH:14]([CH3:16])[CH3:15])=O)C1C=CC=CC=1.CC(OC)(C)C>C(O)(=O)C>[BrH:35].[NH2:12][C@H:13]([C:17]1[O:18][C:19]([C:26]2[C:34]3[C:29](=[C:30]([Br:35])[CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)=[C:20]([C:22]([O:24][CH3:25])=[O:23])[N:21]=1)[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 15413tert-Butyl methyl etherHCID 59595035methyl 2-((S)-1-(benzyloxycarbonylamino)-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate

Product 1

HCID 66889567methyl 2-((S)-1-amino-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate hydrobromideYield 153.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 33% HBr in acetic acid (1.33 L) was added the title compound of Example 5 (403.4 g, 766 mmol) and the stirred vigorously for 1 hour and 20 min. The mixture was slowly and carefully added to MTBE (12 L) with external cooling and strong agitation. The mixture was stirred for 1 hour at 0° C. and filtered under N2. The hygroscopic solids were washed with MTBE (1 L) and dried to constant mass in a vacuum oven to yield the title compound (277.5 g, 76.5%) as a fine brown solid. 1H NMR (CDCl3): consistent with proposed structure.

Workup

  1. temperaturewith external cooling
  2. stirringThe mixture was stirred for 1 hour at 0° C.
  3. filtrationfiltered under N2
  4. washThe hygroscopic solids were washed with MTBE (1 L)
  5. customdried to constant mass in a vacuum oven

Sources & evidence

ORD record
ord-01f361cb86be4320a5eae1291c8048e8
Source dataset
uspto-grants-2009_05
Patent number
US07538129B2

Reaction notes

Loading…