Benzophenone imine → N-(Diphenylmethylene)glycine tert-butyl ester

HRID 2190964Notes

Reaction equation

HRID 2190964 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>ClCCl>[C:2]1([C:1](=[N:14][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzophenone imine (106.2 g; 587 mmol) and tert-butyl 2-aminoacetate hydrochloride (98.3 g; 587 mmol) in dichloromethane (1 L; HPLC grade) was stirred at ambient temperature for 20 hours. The reaction mixture was partitioned between dichloromethane (0.5 L) and water (1.5 L) and the layers were separated. The aqueous phase was extracted with dichloromethane (0.5 L) and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give a slightly off-white solid. The resulting solid was triturated with n-hexane to give 141 g (83.1%) of the title product as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 7.62 (d, 2H, ArH), 7.21-7.42 (m, 6H, ArH), 7.13 (d, 2H, ArH), 4.05 (s, 2H, CH2), 1.41 (s, 9H, C(CH3)3); 13C-NMR (CDCl3, 100 MHz) δ 171.5, 169.8, 139.4, 136.2, 130.4, 128.8, 128.7, 128.6, 128.0, 127.7, 81.4, 56.3, 28.1.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (0.5 L) and water (1.5 L)
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (0.5 L)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a slightly off-white solid
  8. customThe resulting solid was triturated with n-hexane

Sources & evidence

ORD record
ord-52b50626c18a4352a02ee67f068fc14c
Source dataset
uspto-grants-2012_12
Patent number
US08324417B2

Reaction notes

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