Benzyl Alcohol → (S)-benzyl 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid

HRID 75706Notes

Reaction equation

HRID 75706 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[CH2:37](O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:37]([C@:2]([NH:1][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([C:3]([CH3:6])([CH3:5])[CH3:4])[C:7]([OH:9])=[O:8])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 131731871(S)-benzyl 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Boc-Tle-OH (4.8 g, 22.3 mmol) was dissolved in dichloromethane (50 mL), and EDCI (4.3 g, 44.6 mmol), DMAP (0.6 g, 4.46 mmol), DIPEA (16 mL, 89.2 mmol), and benzyl alcohol (5 mL, 44.6 mmol) were added dropwise. The mixture was stirred at room temperature for 12 hours. The mixture was washed several times with an aqueous solution of 5% citric acid. The organic layer was dried over sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound as yellow oil (6.7 g, 99%).

Workup

  1. washThe mixture was washed several times with an aqueous solution of 5% citric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-0811e5819ad94353bf649156dfb9333c
Source dataset
uspto-grants-2014_09
Patent number
US08835458B2

Reaction notes

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