HCID 118574239, compound → HCID 118574255, compound

HRID 1055450Notes

Reaction equation

HRID 1055450 reaction equation
Br[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]([N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:26])[CH3:24])[CH2:17][O:16][C:15]3[C:35]([C:39]([O:41][CH3:42])=[O:40])=[CH:36][CH:37]=[CH:38][C:14]1=3)=[C:7]([O:43][CH3:44])[CH:6]=[CH:5]2>CO.[Pd]>[C:30]([O:29][C:27]([N:25]([CH3:26])[C@@H:23]([CH3:24])[C:22]([NH:21][C@H:18]1[CH2:17][O:16][C:15]2[C:35]([C:39]([O:41][CH3:42])=[O:40])=[CH:36][CH:37]=[CH:38][C:14]=2[N:13]([CH2:12][C:8]2[C:9]3[C:4](=[CH:3][CH:2]=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]=2[O:43][CH3:44])[C:19]1=[O:20])=[O:34])=[O:28])([CH3:32])([CH3:33])[CH3:31]

Participants

4

Reactant 1

HCID 118574239HCID 118574239, compound

Product 1

HCID 118574255HCID 118574255, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-methyl 5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylate (100 mg, 149 μmol, Eq: 1.00) and 10% Pd/C (5.22 mg, 4.92 μmol, Eq: 0.033) in MeOH (5 mL) was hydrogenated at RT overnight. The mixture was filtered through Celite and the filtrate concentrated to afford (S)-methyl 3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-5-((2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylate (95 mg, 97%) as a tan foam.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-2e14ff7c8cd94f63adb6854e909656dd
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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