Diethyl Ether → HCID 68767912, compound

HRID 1171561Notes

Reaction equation

HRID 1171561 reaction equation
[CH:1]([N:4]([CH3:33])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16]C(=O)OCC3C=CC=CC=3)[C:12]2=[O:27])[C@H:7]([CH2:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:6]1)([CH3:3])[CH3:2].CCOCC>Br.CC(O)=O>[NH2:16][C@H:13]1[CH2:14][CH2:15][N:11]([C@H:8]2[CH2:9][CH2:10][C@@H:5]([N:4]([CH:1]([CH3:3])[CH3:2])[CH3:33])[CH2:6][C@H:7]2[CH2:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:12]1=[O:27]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 86596884HCID 86596884, compound

Product 1

HCID 68767912HCID 68767912, compoundYield 121.5%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

The material from above benzyl (S)-1-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(methylsulfonylmethyl)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (600 mg) was dissolved in 33% HBr/AcOH (10 mL) at rt. The solution was stirred for 30 min before Et2O was added. This resulted in a precipitate which was isolated to afford the bis-hydrogen bromide salt of (S)-3-amino-1-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(methylsulfonylmethyl)cyclohexyl)pyrrolidin-2-one (525 mg). MS found: (M+H)+=346.5.

Workup

  1. additionwas added
  2. customThis resulted in a precipitate which
  3. customwas isolated

Sources & evidence

ORD record
ord-8096f2211fbf4294a4cb20b5c9072b5f
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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