HCID 86677203, compound → HCID 86677202, compound

HRID 403452Notes

Reaction equation

HRID 403452 reaction equation
[NH2:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][C@@H:7]2[CH2:11][CH2:10][C@H:9]([C@H:12]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:4][C:3]=1[N+:36]([O-])=O>C(O)(=O)C.[Zn]>[Si:20]([O:19][C@H:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C@H:9]1[CH2:10][CH2:11][C@@H:7]([CH2:6][C:5]2[CH:34]=[CH:35][C:2]([NH2:1])=[C:3]([NH2:36])[CH:4]=2)[N:8]1[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 86677203HCID 86677203, compound

Product 1

HCID 86677202HCID 86677202, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 0.58 g (1.1 mmol) of tert-butyl(2S,5R)-2-(4-amino-3-nitrobenzyl)-5-[(R)-{[tertbutyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate from Step A in 5 mL of acetic acid was added 0.35 g (5.4 mmol) of zinc dust and the resulting mixture was stirred under nitrogen for 1 h. The reaction mixture was then filtered through a pad of Celite. The pad was washed with dichloromethane (3×25 mL) and the combined filtrates were concentrated in vacuo. The crude residue was purified by reverse-phase HPLC (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to afford the title compound as a yellow solid. LC/MS: m/z (ES) 512.3 (MH)+.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite
  2. washThe pad was washed with dichloromethane (3×25 mL)
  3. concentrationthe combined filtrates were concentrated in vacuo
  4. customThe crude residue was purified by reverse-phase HPLC (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)

Sources & evidence

ORD record
ord-cd95351dd0d54f09bc3d7625cf13e1ce
Source dataset
uspto-grants-2014_06
Patent number
US08748433B2

Reaction notes

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