Acetohydrazide → HCID 57637130, compound

HRID 1804556Notes

Reaction equation

HRID 1804556 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:17][NH2:18])(=[O:16])[CH3:15].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=C[C:27]=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1.ClCCl>[O:13]=[C:11]([NH:18][NH:17][C:14](=[O:16])[CH2:15][CH3:27])[CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 14039AcetohydrazideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 57637130HCID 57637130, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

25.00 g (132 mmol) 3-tert-butoxycarbonylamino-propionic acid, 11.45 g (130 mmol) ethanoic 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 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 isopropylether

Sources & evidence

ORD record
ord-178f1cf8d6bb43d8b6ec67fa9e3b3455
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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