(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 → (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

HRID 1055480Notes

Reaction equation

HRID 1055480 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:33][CH3:34])[C:4]([NH:6][C@H:7]1[CH2:13][O:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[N:9]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([Br:29])=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[O:30][CH3:31])[C:8]1=[O:32])=[O:5]>CO.C(Cl)Cl>[NH2:2][C@@H:3]([CH2:33][CH3:34])[C:4]([NH:6][C@H:7]1[CH2:13][O:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[N:9]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([Br:29])=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[O:30][CH3:31])[C:8]1=[O:32])=[O:5]

Participants

3

Reactant 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 hydrochloride

Product 1

HCID 90036882(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)butanamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of (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 (283 mg) in 25% MeOH/CH2Cl2 was treated with silica-supported carbonate (SiliCycle, 3 eq) for 1 h, filtered, and the filtrate concentrated 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 (264 mg) as a white foam. MS m/z 512/514 (MH)+

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f8143d577f6d4895afbe58660822e69c
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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