1-(Bromomethyl)-4-chlorobenzene → (S)-N-((S)-5-(4-Chlorobenzyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamide

HRID 1055449Notes

Reaction equation

HRID 1055449 reaction equation
C[N:2]([C@@H:10]([CH3:26])[C:11](=[O:25])[NH:12][C@H:13]1[CH2:19][O:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[NH:15][C:14]1=[O:24])[C:3](=O)OC(C)(C)C.Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1>>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:15]2[C:14](=[O:24])[C@@H:13]([NH:12][C:11](=[O:25])[C@@H:10]([NH:2][CH3:3])[CH3:26])[CH2:19][O:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]2=3)=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 72713380tert-Butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate

Product 1

HCID 73054591(S)-N-((S)-5-(4-Chlorobenzyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamideYield 61.2%

Procedure

In a similar manner to that described for Example 45 except in Step 2 the material obtained after chromatography was not triturated, tert-butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate (173 mg, 476 iumol) and 1-(bromomethyl)-4-chlorobenzene (103 mg, 500 μmol) were converted to the title compound (113 mg) as an off-white foam. HRMS: calcd. for C20H22N3O3Cl: (MH+) 388.1422. found 388.1423.

Workup

  1. customobtained after chromatography
  2. customwas not triturated

Sources & evidence

ORD record
ord-618ec1e34baf498893aa24c173b2225d
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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