2-Methylpropanehydrazide → tert-butyl [3-(N'-isobutyryl-hydrazino)-3-oxo-propyl]-carbamate

HRID 1804563Notes

Reaction equation

HRID 1804563 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]([NH:19][NH2:20])(=[O:18])[CH:15]([CH3:17])[CH3:16].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>O1CCCC1.ClCCl>[C:14]([NH:19][NH:20][C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:18])[CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 192392-MethylpropanehydrazideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 57637099tert-butyl [3-(N'-isobutyryl-hydrazino)-3-oxo-propyl]-carbamate

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

25.00 g (132 mmol) 3-tert-butoxycarbonylamino-propionic acid, 13.50 g (132 mmol) isobutyric acid hydrazide, 50.91 g (159 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) and 50 ml diisopropylethylamine are stirred in 500 ml of tetrahydrofuran/dichloromethane for 24 hours at ambient temperature. Then the mixture is evaporated down, the residue is extracted with ethyl acetate and 10% potassium hydrogen carbonate solution. The organic phase is dried and evaporated to dryness. The residue is crystallised from toluene/isopropylether.

Workup

  1. customThen the mixture is evaporated down
  2. extractionthe residue is extracted with ethyl acetate and 10% potassium hydrogen carbonate solution
  3. customThe organic phase is dried
  4. customevaporated to dryness
  5. customThe residue is crystallised from toluene/isopropylether

Sources & evidence

ORD record
ord-0ff5658c05f743d988f8ea51d2fca0ca
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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