Hydrochloric Acid → (3S)-3-amino-9-phenyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride

HRID 1670433Notes

Reaction equation

HRID 1670433 reaction equation
[ClH:1].[O:2]=[C:3]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[O:6][CH2:5][C@@H:4]1[NH:20]C(=O)OC(C)(C)C>O1CCOCC1>[ClH:1].[NH2:20][C@@H:4]1[C:3](=[O:2])[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:7]=2[O:6][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86628748tert-butyl [(3S)-4-oxo-9-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]carbamate

Product 1

HCID 67328839(3S)-3-amino-9-phenyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.4 mL of a solution of hydrochloric acid in dioxane (4M) are added to a 25 mL round-bottomed flask containing 160 mg of 37 (0.452 mmol). The mixture is stirred for 4 h at RT under argon. The dioxane is concentrated, and taken up in 15 mL of isopropyl ether. The solid formed is disintegrated. 113 mg of amine 38 (cream-coloured solid) are obtained after filtration in hydrochloride form.

Workup

  1. concentrationThe dioxane is concentrated
  2. customThe solid formed

Sources & evidence

ORD record
ord-83de2da5b1924fdfa043bc0e6ab760bf
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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