Sodium Hydroxide → HCID 131726191, compound

HRID 2053704Notes

Reaction equation

HRID 2053704 reaction equation
C(O)(=O)[C@H](C1C=CC=CC=1)O.[NH2:12][C@@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=2)[CH2:15][C@H:14]1[OH:25].[OH-].[Na+].[C:28]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=[CH:32][C:31]([C:34](Cl)=[O:35])=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[N+:22]([C:19]1[CH:20]=[C:21]2[C:16]([CH2:15][CH:14]([OH:25])[C@@H:13]2[NH:12][C:34]([C:31]2[CH:32]=[CH:33][C:28]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:29][CH:30]=2)=[O:35])=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 841514-Phenylbenzoyl chlorideHCID 131726751HCID 131726751, compound

Product 1

HCID 131726191HCID 131726191, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add 1(R)-amino-2(R)-hydroxy-6-nitroindane (S)-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-5562ba44cc664fa1ab0b693000cdbeaf
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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