Diisobutylamine → HCID 86653692, compound

HRID 1478936Notes

Reaction equation

HRID 1478936 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:13]([NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH:14]([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:13]([N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:10](=[O:12])[CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 8085DiisobutylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 86653692HCID 86653692, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-Boc-glycine (1.0 g, 5.7 mmol) in DMF (10 ml) were added diisobutylamine (0.10 ml, 11.4 mmol), DIPEA (1.9 ml, 11.4 mmol) and TBTU (2.7 g, 8.5 mmol). The mixture was stirred for 1 hr at room temperature, quenched with saturated aqueous sodium bicarbonate (15 ml), and extracted with EtOAc (20 ml). The organic phase was washed with brine (15 ml), dried over anhydrous MgSO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (30% EtOAc in hexanes) to provide tert-butyl 2-(diisobutylamino)-2-oxoethylcarbamate (1.6 g, 98%) as a colorless oil. [M+H]+ 287.3, HPLC purity: 90%.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate (15 ml)
  2. extractionextracted with EtOAc (20 ml)
  3. washThe organic phase was washed with brine (15 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8d3972816fdf4deabb6e856a1abb59af
Source dataset
uspto-grants-2016_08
Patent number
US09403789B2

Reaction notes

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