Triethylamine → ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester

HRID 446947Notes

Reaction equation

HRID 446947 reaction equation
O.[C:2]([NH:9][C@@H:10]([C:15]([OH:17])=O)[CH2:11][CH:12]([CH3:14])[CH3:13])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[CH2:18]([N:20](CC)[CH2:21]C)C.Cl.CNC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:5]([O:4][C:2](=[O:3])[NH:9][C@@H:10]([C:15](=[O:17])[N:20]([CH3:21])[CH3:18])[CH2:11][CH:12]([CH3:14])[CH3:13])([CH3:8])([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2724699PyBOPHCID 2724763BOC-D-LEU-OH H2O

Product 1

HCID 28165661((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl esterYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Boc-D-leucine monohydrate (2.0 g, 8.0 mmol), triethylamine (5.6 mL, 40.1 mmol), and dimethylamine hydrochloride (1.31 g, 16.0 mmol) in DMF (15 mL) at room temperature was added PyBOP (4.59 g, 8.82 mmol). The reaction mixture was stirred overnight then diluted with EtOAc (50 mL) and washed with water (4×50 mL). The combined organic extracts were dried (Na2SO4) and evaporated under vacuum. The crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1) to give 1.19 g (58%) of ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester as a colorless viscous oil.

Workup

  1. washwashed with water (4×50 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customevaporated under vacuum
  4. customThe crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-948d16f949124e3abb92073d9e0fda0f
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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