3-[5-(3,5-bis-Trifluoromethyl-benzoyl)-2-nitro-phenyl]-2-tert-butoxycarbonylamino-propionic Acid Tert-Butyl Ester → 3-[2-Amino-5-(3,5-bis-Trifluoromethyl-benzoyl)-phenyl]-2-tert-butoxycarbonylamino-propionic Acid Tert-Butyl Ester

HRID 1242860Notes

Reaction equation

HRID 1242860 reaction equation
[C:1]([O:5][C:6](=[O:42])[CH:7]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:8][C:9]1[CH:14]=[C:13]([C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:31]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)(C)C>[C:1]([O:5][C:6](=[O:42])[CH:7]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:8][C:9]1[CH:14]=[C:13]([C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:17]=2)[CH:12]=[CH:11][C:10]=1[NH2:31])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 865911703-[5-(3,5-bis-Trifluoromethyl-benzoyl)-2-nitro-phenyl]-2-tert-butoxycarbonylamino-propionic Acid Tert-Butyl Ester

Product 1

HCID 865911693-[2-Amino-5-(3,5-bis-Trifluoromethyl-benzoyl)-phenyl]-2-tert-butoxycarbonylamino-propionic Acid Tert-Butyl EsterYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent2×

Procedure

The nitrobenzophenone derivative 52 (0.7475 g, 1.23 mmol), isopropanol (40 mL), and 10% palladium on activated carbon (131 mg, 0.131 mmol) were added to a single-necked 200 mL pear-shaped round-bottom flask. The flask was sealed with a rubber septum and charge-purged three times using a hydrogen-filled balloon followed by house vacuum. The reaction vessel was equipped with two hydrogen-filled balloons and allowed to stir at room temperature for exactly 15 minutes. During this time a filter funnel was prepared with celite and packed with isopropanol. The reaction mixture was immediately vacuum filtered through the funnel into a 100 mL round-bottom flask. The solvent was removed in vacuo and the crude mixture was purified by flash chromatography (20% EtOAc:hexanes) to afford 58 as a yellow solid (0.631 g, 89%): m.p. 134–135° C.

Workup

  1. customThe flask was sealed with a rubber septum
  2. customcharge-purged three times
  3. additionfilled balloon
  4. customThe reaction vessel was equipped with two hydrogen-
  5. additionfilled balloons
  6. customDuring this time a filter funnel was prepared with celite
  7. filtrationfiltered through the funnel into a 100 mL round-bottom flask
  8. customThe solvent was removed in vacuo
  9. customthe crude mixture was purified by flash chromatography (20% EtOAc:hexanes)

Sources & evidence

ORD record
ord-b0d77fdba2e64b52965f5b8e75e905af
Source dataset
uspto-grants-2006_10
Patent number
US07115766B2

Reaction notes

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