Diisobutylaluminum hydride → 2,2-Bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl ester

HRID 79704Notes

Reaction equation

HRID 79704 reaction equation
CC(C[AlH]CC(C)C)C.[CH2:10]([O:17][C:18](=[O:44])[C:19]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:20][CH2:21][C:22](=[O:27])N(OC)C)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCCCCC>[CH2:10]([O:17][C:18](=[O:44])[C:19]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([NH:36][C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH2:20][CH2:21][CH:22]=[O:27])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 866488752,2-Bis(tert-butoxycarbonylamino)-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester

Product 1

HCID 866488762,2-Bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl esterYield 75.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of DIBAL (1.0 M, 14.7 mL, 14.7 mmol) in hexane was added dropwise to a solution of 2,2-bis(tert-butoxycarbonylamino)-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester (4 g, 10.5 mmol) under an atmosphere of nitrogen at −78° C. After 2 hours the mixture was quenched with saturated ammonium chloride (30 mL) and allowed to warm to room temperature. Water (20 mL) was added, and the mixture was extracted with diethyl ether (3×50 mL). The combined organic phases were left to stand at room temperature for 15 minutes. The resulting thick gel was filtered through a pad of CELITE. The filtrate was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure to provide 2,2-bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl ester (3.34 g, 7.9 mmol, 75%). This was used immediately in the next step.

Workup

  1. customAfter 2 hours the mixture was quenched with saturated ammonium chloride (30 mL)
  2. additionWater (20 mL) was added
  3. extractionthe mixture was extracted with diethyl ether (3×50 mL)
  4. waitThe combined organic phases were left
  5. filtrationThe resulting thick gel was filtered through a pad of CELITE
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e871b63dd63f41828df9a0e18ab0dd26
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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