Diisopropylethylamine → tert-Butyl [(S)-2-allyloxycarbamoyl-2-(4-isobutyrylpiperazin-1-yl)ethyl]carbamate

HRID 874590Notes

Reaction equation

HRID 874590 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:32]([O:36][C:37]([NH:39][CH2:40][C@H:41]([N:45]1[CH2:50][CH2:49][N:48]([C:51](=[O:55])[CH:52]([CH3:54])[CH3:53])[CH2:47][CH2:46]1)[C:42](O)=[O:43])=[O:38])([CH3:35])([CH3:34])[CH3:33].Cl.[CH2:57]([O:60][NH2:61])[CH:58]=[CH2:59].C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:57]([O:60][NH:61][C:42]([C@@H:41]([N:45]1[CH2:50][CH2:49][N:48]([C:51](=[O:55])[CH:52]([CH3:53])[CH3:54])[CH2:47][CH2:46]1)[CH2:40][NH:39][C:37](=[O:38])[O:36][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:43])[CH:58]=[CH2:59]

Participants

8

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 66870931(S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoic acid

Product 1

HCID 86689278tert-Butyl [(S)-2-allyloxycarbamoyl-2-(4-isobutyrylpiperazin-1-yl)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.4 g (4.4 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumtetrafluoroborate and then 2.3 ml (13.1 mmol) of diisopropylethylamine are added to a solution of 1.5 g (4.4 mmol) of (S)-3-tert-butoxycarbonylamino-2-(4-isobutyrylpiperazin-1-yl)propanoic acid in 20 ml of dimethylformamide. After stirring at ambient temperature for 15 min, a solution of 500 mg (4.6 mmol) of O-allylhydroxylamine hydrochloride and of 0.8 ml (4.6 mmol) of diisopropylethylamine in 10 ml of dimethylformamide is added. The reaction medium is stirred at ambient temperature for 20 h, hydrolyzed with a saturated aqueous solution of sodium hydrogen carbonate, and then diluted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum, 1.45 g (83%) of tert-butyl [(S)-2-allyloxycarbamoyl-2-(4-isobutyrylpiperazin-1-yl)ethyl]carbamate are obtained in the form of a colorless oil.

Workup

  1. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum, 1.45 g (83%) of tert-butyl [(S)-2-allyloxycarbamoyl-2-(4-isobutyrylpiperazin-1-yl)ethyl]carbamate
  5. customare obtained in the form of a colorless oil

Sources & evidence

ORD record
ord-ba0905c27a9043388f6e4a639fd2750f
Source dataset
uspto-grants-2015_03
Patent number
US08980897B2

Reaction notes

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