Citric Acid → HCID 58778279, compound

HRID 1371565Notes

Reaction equation

HRID 1371565 reaction equation
[C:1]([N:8](C1C=CC=CC=1)CC=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:18][O:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+].[C:41](O)(=O)[CH2:42][C:43]([CH2:48][C:49](O)=O)([C:45](O)=O)O>ClCCl.C(OCC)(=O)C>[CH3:18][O:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][CH2:49][CH:48]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[C:43]1[CH:42]=[CH:41][CH:28]=[CH:27][CH:45]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 70002-MethoxyanilineHCID 5049666Sodium triacetoxyborohydrideHCID 15168496tert-Butyl (2-oxoethyl)phenylcarbamate

Product 1

HCID 58778279HCID 58778279, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boc-phenylglycinal (0.74 g, 3.1 mmol) and 2-methoxyaniline (0.40 g, 3.3 mmol) were combined in dichloromethane and sodium triacetoxyborohydride (0.80 g, 3.8 mmol) was added as a solid. The reaction mixture was stirred at room temperature for 4 hours, diluted with 10% citric acid and ethyl acetate, and the organic layer was then washed with saturated sodium bicarbonate, washed with brine, dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography on silica (0 to 30% EtOAc/hexanes) to give a white foam, 0.54 g, 1.6 mmol, 51% yield. 1H NMR (500 MHz, CDCl3) δ 7.31–7.21 (m, 5H), 6.78 (m, 1H), 6.68 (m, 1H), 6.60 (m, 2H), 5.04 (br s, 1H), 4.89 (br s, 1H), 4.32 (br s, 1H), 3.71 (s, 3H), 3.39 (m, 2H), 1.35 (s, 9H).

Workup

  1. washthe organic layer was then washed with saturated sodium bicarbonate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to an oil, which
  5. customwas purified by column chromatography on silica (0 to 30% EtOAc/hexanes)
  6. customto give a white foam, 0.54 g, 1.6 mmol, 51% yield

Sources & evidence

ORD record
ord-de191283b34c40fe8d9d0a8d31aeb777
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

Loading…