Diethyl Ether → HCID 68765539, compound

HRID 1374334Notes

Reaction equation

HRID 1374334 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]1[CH2:14][C@H:13]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:12][CH2:11][C@@H:10]1[N:20]1[CH2:24][CH2:23][C@H:22]([NH:25]C(=O)OCC2C=CC=CC=2)[C:21]1=[O:36])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].CCOCC>Br.CC(O)=O.CCOC(C)=O>[NH2:25][C@H:22]1[CH2:23][CH2:24][N:20]([C@H:10]2[CH2:11][CH2:12][C@@H:13]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:14][C@H:9]2[CH2:8][S:5]([C:1]([CH3:2])([CH3:4])[CH3:3])(=[O:7])=[O:6])[C:21]1=[O:36]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 86596888HCID 86596888, compound

Product 1

HCID 68765539HCID 68765539, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

The material from above benzyl (S)-1-((1S,2R,4R)-2-(tert-butylsulfonylmethyl)-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (1.0 g) was dissolved in 33% HBr/AcOH (5 mL) at rt. The solution was stirred for 30 min before Et2O was added. This resulted in a precipitate which was isolated. The solid was dissolved in EtOAc and was washed with sat. Na2CO3 solution. The organic phase was dried (MgSO4), filtered, and concentrated to afford (S)-3-amino-1-((1S,2R,4R)-2-(tert-butylsulfonylmethyl)-4-(isopropyl(methyl)amino)cyclohexyl)pyrrolidin-2-one (250 mg). MS found: (M+H)+=388.4.

Workup

  1. additionwas added
  2. customThis resulted in a precipitate which
  3. customwas isolated
  4. washwas washed with sat. Na2CO3 solution
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-473f8bc8a1fa417a9ad139443ae00238
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

Loading…