Water → HCID 89648245, compound

HRID 2281010Notes

Reaction equation

HRID 2281010 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([NH:13]C(OCC[Si](C)(C)C)=O)[CH:10]([C:23](=[O:32])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>CCOCC>[NH2:13][CH:11]1[CH:10]([C:23](=[O:32])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 89647587HCID 89647587, compound

Product 1

HCID 89648245HCID 89648245, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 3-(3-Fluoro-phenylcarbamoyl)-4-(2-trimethylsilanyl-ethoxycarbonylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (1700.00 mg; 3.64 mmol; 1.00 eq.) was added of TBAF (2851.67 mg; 10.91 mmol; 3.00 eq.) (1.0M in THF 11 ml). The resulting mixture was stirred overnight. The reaction mixture was poured into water, washed with brine, then 5% NaHCO3, brine, dried and concentrated to give the crude, which was added of ether (5 ml). The precipitated white solid was filtered to afford the title compound (710 mg, 60.4%).

Workup

  1. washwashed with brine
  2. dry with material5% NaHCO3, brine, dried
  3. concentrationconcentrated
  4. customto give the crude, which
  5. filtrationThe precipitated white solid was filtered

Sources & evidence

ORD record
ord-7da8780d85ea4364b7ee9ab82b346824
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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