Benzhydrylamine → HCID 21998158, compound

HRID 1977492Notes

Reaction equation

HRID 1977492 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[NH2:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[C:15]1([CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:7][CH:3]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:2]([OH:6])=[O:5])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 66827Phenylboronic AcidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 21998158HCID 21998158, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of glyoxylic acid monohydrate (92 mg, 1 mmol) in dichloromethane (7 mL) was added aminodiphenylmethane (183 mg, 1 mmol), followed by phenylboronic acid (122 mg, 1 mmol). After the flask was purged with argon and sealed, the reaction mixture was stirred vigorously at room temperature for 48 h. The resulting precipitate was isolated by filtration, washed with dichloromethane (10 mL) and purified by ion-exchange chromatography (Dowex 50W-X8) to give pure (±)-N-(diphenylmethyl)-α-phenylglycine (266 mg, 84% yield).

Workup

  1. customAfter the flask was purged with argon
  2. customsealed
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed with dichloromethane (10 mL)
  5. custompurified by ion-exchange chromatography (Dowex 50W-X8)

Sources & evidence

ORD record
ord-61843cf72a83446ea3c43395d1058ee2
Source dataset
uspto-grants-2001_05
Patent number
US06232467B1

Reaction notes

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