Tetrahydrofuran → HCID 22674611, compound

HRID 1006320Notes

Reaction equation

HRID 1006320 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:34])[NH:13][CH:14]([CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15]([NH:17][CH2:18]OC)=O)([CH3:10])([CH3:9])[CH3:8].[OH-:35].[Na+].[O:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH2:38]([O:37][C:41](=[O:35])[CH2:40][N:17]([CH2:18][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][CH:14]([NH:13][C:12]([O:11][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:34])[CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:39]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69819924HCID 69819924, compound

Product 1

HCID 22674611HCID 22674611, compound

Procedure

Lithium aluminum hydride (114 mg) was added by small portions to an ice-cooled solution of 1-benzhydryl-2-(N-methoxymethylamino)-2-oxoethylcarbamic acid tert-butyl ester (1.15 g) in tetrahydrofuran (10 ml) below 5° C. under nitrogen atmosphere. After the mixture was stirred at the same temperature for 1 hour, 2N sodium hydroxide (0.5 ml) was added to the mixture. After the mixture was stirred for 30 minutes, the insoluble materials were removed by filtration and washed with tetrahydrofuran. The filtrate and the washing were combined, and evaporated under reduced pressure. The residue was dissolved into dichloromethane (15 ml), and N-benzylglycine ethyl ester (609 mg) was added to the solution. To the resulting solution sodium triacetoxyborohydride (1.27 g) was added portionwise under stirring and the whole was stirred at 5° C.˜room temperature overnight. The mixture was partitioned between ethyl acetate and 2N sodium hydroxide. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give N-benzyl-N-[2-(tert-butoxycarbonylamino)-3,3-diphenylpropyl]glycine ethyl ester (1.51 g) as a colorless oil.

Workup

  1. stirringAfter the mixture was stirred for 30 minutes
  2. customthe insoluble materials were removed by filtration
  3. washwashed with tetrahydrofuran
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved into dichloromethane (15 ml), and N-benzylglycine ethyl ester (609 mg)
  6. additionwas added to the solution
  7. additionTo the resulting solution sodium triacetoxyborohydride (1.27 g) was added portionwise
  8. stirringunder stirring
  9. stirringthe whole was stirred at 5° C.˜room temperature overnight
  10. customThe mixture was partitioned between ethyl acetate and 2N sodium hydroxide
  11. customThe organic layer was separated
  12. washwashed with brine
  13. dry with materialdried over sodium sulfate
  14. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-764ee4a6a2f4420cac03be57f85d8ef4
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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