Acetone → HCID 68685786, compound

HRID 638957Notes

Reaction equation

HRID 638957 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][NH:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:23]CN(C(C)C)C(C)C.CCOCC.[CH3:37][C:38]([CH3:40])=[O:39]>>[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]([CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:37][C:38](=[O:39])[CH2:40][CH3:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 180Acetone2×HCID 3283Diethyl EtherHCID 81531Diisopropylethylamine2×HCID 11087797tert-Butyl N-(diphenylmethyl)glycinate

Product 1

HCID 68685786HCID 68685786, compoundYield 98%

Procedure

To a solution of (benzhydrylamino)acetic acid tert-buyl ester (6.1 g, 20.5 mmol, 1 eq.) in dry acetone (75 mL) at −50° C. to −60° C. was added DIEA (3.58 mL, 20.5 mmol, 1 eq.) followed by a solution of 1-bromobuta-2-none (2.33 mL, 20.5 mmol, 1 eq.) in acetone (75 mL). The reaction mixture was allowed to warm to room temperature and then heated to reflux for 2 h. The reaction was cooled and then added additional 5% (by weight) of DIEA and 1-bromobuta-2-none. The resulting mixture was continued to be heated at reflux overnight. The reaction mixture was cooled to room temperature and added Et2O. The precipitated solid was filtered off and washed with Et2O. The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford [benzhydryl-(2-oxobutyl)amino]acetic acid tert-butyl ester in 98% yield (crude product), which was used without further purification. ESMS: m/z 368.4 [M+H].

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperatureThe reaction was cooled
  4. temperatureto be heated
  5. temperatureat reflux overnight
  6. temperatureThe reaction mixture was cooled to room temperature
  7. filtrationThe precipitated solid was filtered off
  8. washwashed with Et2O
  9. washThe combined organic layer was washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43abbccad82f4cbcb37647e17224f927
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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