HCID 78035248, compound → HCID 86675578, compound

HRID 1422590Notes

Reaction equation

HRID 1422590 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]12[CH2:18][CH:17]1[CH2:16][CH2:15][S:14][C:13]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:12]2.[H][H]>CO.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:11]23[CH2:18][CH:17]2[CH2:16][CH2:15][S:14][C:13]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[N:12]3)[CH:4]=1

Participants

5

Reactant 2

HCID 78035248HCID 78035248, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86675578HCID 86675578, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

tert-Butyl (1SR,7SR)-1-(2-fluoro-5-nitrophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (intermediate rac-A7a) (68 mg; 0.18 mmol) was dissolved in 20 ml methanol under argon and 10% palladium on carbon (Pd/C) (28 mg, 15 mol %) was added. The atmosphere of the reaction system was replaced with hydrogen, followed by stiffing at 23° C. for 3 hours. More 10% Pd/C (67 mg) was added and stiffing was continued under hydrogen atmosphere for 20 hours. The reaction mixture was filtered and evaporated to give the tert-butyl (1SR,7SR)-1-(5-amino-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (53 mg; 85%) as a grey foam which was used in the next step without further purification. MS (ISP): m/z=352.3 [(M+H)+].

Workup

  1. waitstiffing was continued under hydrogen atmosphere for 20 hours
  2. filtrationThe reaction mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-fba911b6390e4a4885d70ea961429102
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

Loading…