Toluene → [1-(6-Fluoro-3,4-dihydro-5-oxa-1,2a-diaza-acenaphthylen-2-yl)ethyl]carbamic acid tert-butyl ester

HRID 243223Notes

Reaction equation

HRID 243223 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[C:17]2[NH:18][CH2:19][CH2:20][O:21][C:16]=2[C:15]([F:22])=[CH:14][CH:13]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.FC1C=CC2=C3C=1OCCN3C(C(NC(=O)C)C)=N2>CC(O)=O>[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([C:10]1[N:18]2[C:17]3[C:16]([O:21][CH2:20][CH2:19]2)=[C:15]([F:22])[CH:14]=[CH:13][C:12]=3[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 68156926N-[1-(6-fluoro-3,4-dihydro-5-oxa-1,2a-diaza-acenaphthylen-2-yl)ethyl]acetamideHCID 68158273[(S)-1-(8-Fluoro-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157787[1-(6-Fluoro-3,4-dihydro-5-oxa-1,2a-diaza-acenaphthylen-2-yl)ethyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(8-fluoro-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (440 mg, 1.297 mmol) in AcOH (15 mL) was stirred successively at 80° C. for 1 h, 100° C. for 5 h and then 85° C. for 16 h. Toluene was added and the reaction mixture concentrated in vacuo to give a mixture of the title compound and N-[1-(6-fluoro-3,4-dihydro-5-oxa-1,2a-diaza-acenaphthylen-2-yl)ethyl]acetamide. LCMS (Method B): RT 1.72 min [M+H]+ 264 & 2.51 min [M+H]+ 322

Workup

  1. concentrationthe reaction mixture concentrated in vacuo
  2. customto give

Sources & evidence

ORD record
ord-2441fb3906554d509272ce3a4a61d8a5
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…