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Hydrochloric Acid → (S)-N-((S)-5-((6-Bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydro benzo[b][1,4]oxazepin-3-yl)-2-(methylamino)butanamide hydrochloride

HRID 1055477
Notes
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Reaction equation

HRID 1055477 reaction equation
[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH2:13][N:14]1[C:20](=[O:21])[C@@H:19]([NH:22][C:23](=[O:36])[C@@H:24]([N:27](C)[C:28](=O)OC(C)(C)C)[CH2:25][CH3:26])[CH2:18][O:17][C:16]3[CH:37]=[CH:38][CH:39]=[CH:40][C:15]1=3)=[C:8]([O:41][CH3:42])[CH:7]=[CH:6]2>CCOCC.CO>[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH2:13][N:14]1[C:20](=[O:21])[C@@H:19]([NH:22][C:23](=[O:36])[C@@H:24]([NH:27][CH3:28])[CH2:25][CH3:26])[CH2:18][O:17][C:16]3[CH:37]=[CH:38][CH:39]=[CH:40][C:15]1=3)=[C:8]([O:41][CH3:42])[CH:7]=[CH:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131736373tert-butyl (S)-1-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxobutan-2-yl(methyl)carbamate

Product 1

HCID 72943441(S)-N-((S)-5-((6-Bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydro benzo[b][1,4]oxazepin-3-yl)-2-(methylamino)butanamide hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

2 M HCl in Et2O (419 μL) was added to a solution of tert-butyl (S)-1-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxobutan-2-yl(methyl)carbamate (65.7 mg, 105 μmol) in MeOH (105 μL). After 4 h the mixture was concentrated and the residue was dissolved in MeCN/H2O and the solution lyophilized to provide the title compound (55.9 mg, 95%) as a white solid. MS m/z 526/528 (MH)′

Workup

  1. concentrationAfter 4 h the mixture was concentrated
  2. dissolutionthe residue was dissolved in MeCN/H2O

Sources & evidence

ORD record
ord-3d34a2146d2944e392b86a5281cee991
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes