Water → tert-butyl 2-(4-amino-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetate

HRID 923600Notes

Reaction equation

HRID 923600 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([C:19]4[CH:45]=[CH:44][C:22]([CH2:23][N:24]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:25](=[O:35])[C:26]5[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=5)=[CH:21][CH:20]=4)[N:15]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.[Cl-].[Na+].O>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]([N:24]([CH2:36][C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH2:23][C:22]2[CH:21]=[CH:20][C:19]([C:16]3[N:15]=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([C:5]5[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=5)=[CH:9][CH:10]=4)[O:18][N:17]=3)=[CH:45][CH:44]=2)=[O:35])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 71111626tert-butyl 2-(N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate

Product 1

HCID 89284998tert-butyl 2-(4-amino-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetateYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

Prepared using General Procedure 5. To a stirred solution of tert-butyl 2-(N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-58 (7.25 g, 12.0 mmol) in THF (30 mL) was added water (10 mL) and sodium dithionite (6.26 g, 36.0 mmol) and then heated to 65° C. for 3 h. The reaction mixture was allowed to cool to room temperature and then diluted with brine (300 mL) and extracted into EA (300 mL) and THF (250 mL). The combined organics were dried over MgSO4 and concentrated in vacuo. The solid was dried under vacuum for 18 h to afford 7.17 g (100%.) of tert-butyl 2-(4-amino-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetate INT-59 as a pale yellow powder. LCMS-ESI (m/z) calculated for C35H34N4O4: 574; found 519 [M-t-Bu+H]+, tR=3.12 min (Method 10).

Workup

  1. customPrepared
  2. temperatureto cool to room temperature
  3. extractionextracted into EA (300 mL) and THF (250 mL)
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe solid was dried under vacuum for 18 h

Sources & evidence

ORD record
ord-a5e77c7298e34616b334364700935b40
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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