Triethylamine → (S)-methyl 2-((2-((tert-butoxycarbonyl)amino)butyl)amino)-2-oxoacetate

HRID 576696Notes

Reaction equation

HRID 576696 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]([CH2:11][CH3:12])[CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:22](=[O:27])[C:23]([O:25][CH3:26])=[O:24]>C(Cl)Cl.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:7][C@@H:8]([CH2:11][CH3:12])[CH2:9][NH:10][C:22](=[O:27])[C:23]([O:25][CH3:26])=[O:24])=[O:13])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 45091848tert-butyl N-((2S)-1-aminobutan-2-yl)carbamate

Product 1

HCID 90402569(S)-methyl 2-((2-((tert-butoxycarbonyl)amino)butyl)amino)-2-oxoacetateYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To an ice cold solution of (S)-tert-butyl(1-aminobutan-2-yl)carbamate (1.0 g, 5.4 mmol) and triethylamine (0.78 mL, 5.6 mmol) in DCM (33 mL) was added methyl chlorooxoacetate (0.52 mL, 5.6 mmol) dropwise. Following the addition, the reaction was allowed to warm to rt and stirred overnight. Brine was added, the layers were separated, and the aqueous layer was washed with DCM. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to provide a yellow oil (1.4 g, 96%), which was used without further purification. 1H NMR (500 MHz, CDCl3) δ 7.78 (s, 1H), 4.59 (d, J=7.6 Hz, 1H), 3.92-3.81 (m, 3H), 3.69 (s, 1H) 3.45 (dt, J=13.5, 4.2 Hz, 1H), 3.39-3.22 (m, 1H), 1.47-1.38 (m, 11H), 0.98 (t, J=7.5 Hz, 3H).

Workup

  1. additionthe addition
  2. customthe layers were separated
  3. washthe aqueous layer was washed with DCM
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59548730b4f24d85bcea18f3958bb55b
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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