Sodium Hydroxide → HCID 131726191, compound

HRID 1373206Notes

Reaction equation

HRID 1373206 reaction equation
C([O:11][C@@H:12]1[CH2:20][C:19]2[C:14](=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[CH:17][CH:18]=2)[C@H:13]1[NH2:24])(=O)C(C1C=CC=CC=1)O.[OH-].[Na+].[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][C:30]([C:33](Cl)=[O:34])=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[N+:21]([C:16]1[CH:15]=[C:14]2[C:19]([CH2:20][CH:12]([OH:11])[C@@H:13]2[NH:24][C:33]([C:30]2[CH:31]=[CH:32][C:27]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:28][CH:29]=2)=[O:34])=[CH:18][CH:17]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 841514-Phenylbenzoyl chlorideHCID 67523256HCID 67523256, compound

Product 1

HCID 131726191HCID 131726191, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add (1R,2R)-1-amino-6-nitroindan-2-ol mandelate (0.64 kg, 1.85 mol) to a mixture of toluene (9.6 L) and aqueous 1 N NaOH (4.8 L, 4.8 mol, 2.6 equiv). After 1 h, add 4-biphenylcarbonyl chloride (0.44 kg, 2.0 mol, 1.1 equiv) in portions over 20–30 min. After 22 hours, filter the solids under vacuum and rinse sequentially with 0.5 L of toluene, 2 L of water, and 2 L of toluene. Dry the cake to afford 0.74 kg of biphenyl-4-carboxylic acid (R)-(6-nitro-2-hydroxyindan-1-yl)amide. Add 38.2 L of ethyl acetate to 1.914 kg of biphenyl-4-carboxylic acid (R)-(6-nitro-2(R)-hydroxyindan-1-yl)amide prepared in a similar manner. Stir the slurry for 18 h, collect the solid by filtration, dry to afford 1.76 kg of biphenyl-4-carboxylic acid (R)-(6-nitro-2(R)-hydroxyindan-1-yl)amide as a white solid.

Workup

  1. waitAfter 22 hours
  2. filtrationfilter the solids under vacuum
  3. washrinse sequentially with 0.5 L of toluene, 2 L of water, and 2 L of toluene
  4. customDry the cake

Sources & evidence

ORD record
ord-73a1ce66072f4de8976ccfa1cd2384ec
Source dataset
uspto-grants-2007_01
Patent number
US07160922B2

Reaction notes

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