Hydrochloric Acid → (S)-2-amino-N-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)butanamide hydrochloride

HRID 1055479Notes

Reaction equation

HRID 1055479 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:12][N:13]1[C:19](=[O:20])[C@@H:18]([NH:21][C:22](=[O:34])[C@@H:23]([NH:26]C(=O)OC(C)(C)C)[CH2:24][CH3:25])[CH2:17][O:16][C:15]3[CH:35]=[CH:36][CH:37]=[CH:38][C:14]1=3)=[C:7]([O:39][CH3:40])[CH:6]=[CH:5]2.[ClH:41]>O1CCOCC1>[ClH:41].[NH2:26][C@@H:23]([CH2:24][CH3:25])[C:22]([NH:21][C@H:18]1[CH2:17][O:16][C:15]2[CH:35]=[CH:36][CH:37]=[CH:38][C:14]=2[N:13]([CH2:12][C:8]2[C:9]3[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]=2[O:39][CH3:40])[C:19]1=[O:20])=[O:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131736374tert-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-ylcarbamate

Product 1

HCID 90038089(S)-2-amino-N-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)butanamide hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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-ylcarbamate (430 mg, 702 μmol) in 4 M HCl in dioxane (3.51 mL) was stirred at RT for 1 h, and concentrated. the residue was triturated with Et2O to provide (S)-2-amino-N -((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)butanamide hydrochloride (357 mg, 93%) as a white solid.

Workup

  1. concentrationconcentrated
  2. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-13fe29fb863c485aa424d5e2e1279085
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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