HCID 89545331, compound → HCID 89545318, compound

HRID 2283411Notes

Reaction equation

HRID 2283411 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19](=[O:30])[C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[C:22]([CH3:29])[CH:21]=2)[C:13]=1[F:31])[CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Zn]>[C:1]([O:5][C:6](=[O:32])[NH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19](=[O:30])[C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([CH3:29])[CH:21]=2)[C:13]=1[F:31])[CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 89545331HCID 89545331, compound

Product 1

HCID 89545318HCID 89545318, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Step 2 To a solution of {(R)-[4-Chloro-2-fluoro-3-(3-methyl-4-nitro-benzoyl)-phenyl]-cyclopropyl-methyl}-carbamic acid tert-butyl ester (608 mg, 1.31 mmol) from step 1 in acetic acid (15 mL) was added zinc dust (859 mg, 13.1 mmol, 10 eq.) and the reaction stirred for 45 minutes. The reaction mixture was filtered and then the filtrate concentrated. The residue was partitioned between EtOAc (30 mL) and sat. aq. sodium bicarbonate (20 mL). The organic phase then washed with water (20 mL) and brine (10 mL) before it was dried (MgSO4), filtered and then concentrated to give {(R)-[3-(4-amino-3-methyl-benzoyl)-4-chloro-2-fluoro-phenyl]-cyclopropyl-methyl}-carbamic acid tert-butyl ester (570 mg, 1.31 mmol, 100%) as a yellow gum. [M−H]− 431

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was partitioned between EtOAc (30 mL) and sat. aq. sodium bicarbonate (20 mL)
  4. washThe organic phase then washed with water (20 mL) and brine (10 mL) before it
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-429b61944cb645dcab013fbf1508cf60
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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