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

HRID 1689735
Notes
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Reaction equation

HRID 1689735 reaction equation
C(OC([NH:11][C@H:12]([C:16]1[O:17][C:18]([C:25]2[C:33]3[C:28](=[C:29]([Br:34])[CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=1)[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.Br.CC(OC)(C)C>C(O)(=O)C>[BrH:34].[NH2:11][C@H:12]([C:16]1[O:17][C:18]([C:25]2[C:33]3[C:28](=[C:29]([Br:34])[CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=1)[CH:13]([CH3:15])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 198.2%

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent
2×

Conditions

Temperature
25 °C

Procedure

Glacial acetic acid (25 mL) was added to methyl 2-((S)-1-(benzyloxycarbonylamino)-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate (9.99 g, 19.0 mmol) in a 500-mL round-bottom flask fitted with a mechanical stirrer. The suspension was stirred at 25° C. and 33% HBr in acetic acid (50 mL) was added in one portion. The mixture became homogeneous and then a precipitate formed in 5-10 min. After 1 h, MTBE (235 mL) was added and stirring was continued at 25° C. for another 1 h 20 min. The mixture was filtered and the precipitate was washed with MTBE (150 mL). The cream-colored powder was dried under vacuum to give methyl 2-((S)-1-amino-2-methylpropyl)-5-(7-bromo-1H-indol-3-yl)oxazole-4-carboxylate hydrobromide (8.91 g, 99% yield). 1H NMR (300 MHz, DMSO-d6): consistent with proposed structure. MS: m/z=392.0 (M+1).

Workup

  1. customfitted with a mechanical stirrer
  2. customa precipitate formed in 5-10 min
  3. stirringstirring
  4. waitwas continued at 25° C. for another 1 h 20 min
  5. filtrationThe mixture was filtered
  6. washthe precipitate was washed with MTBE (150 mL)
  7. customThe cream-colored powder was dried under vacuum

Sources & evidence

ORD record
ord-cb655ae57e4c4b888a211c346a509788
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153619B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes