Semicarbazide → HCID 86599023, compound

HRID 1643367Notes

Reaction equation

HRID 1643367 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([CH:18]=[O:19])[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O)=[O:6])[CH:2]=[CH2:3].C([O-])(=O)C.[Na+].[NH2:25][NH:26][C:27]([NH2:29])=[O:28]>CO>[CH2:1]([O:4][C:5]([NH:7][C@H:8]([CH:18]=[O:19])[CH2:9][CH2:10][C:11](=[N:25][NH:26][C:27]([NH2:29])=[O:28])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 5196SemicarbazideHCID 517045Sodium AcetateHCID 57163548HCID 57163548, compound

Product 1

HCID 86599023HCID 86599023, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 207a (2.39 g, 8.8 mmol), in MeOH (20 ml) was added sodium acetate (0.72 g, 8.8 mmol) and semicarbazide (0.98 g, 8.8 mmol) stirred overnight, concentrated and diluted with CH2Cl2 (100 ml), washed with water, dried and concentrated. Flash chromatography (2% MeOH in CH2Cl2) afforded 208a (2.10 g, 73%) as an oil: [α]D20 −21 (c 2.55°, CH2Cl2); 1H NMR (CDCl3) δ 9.98 (1H, s), 7.27 (1H, d), 5.8 (1H, m), 5.5 (1H, d), 5.35-5.19 (2H, m), 4.58 (2H, m), 4.14 (1H, m), 2.37 (2H, t), 2.09 (1H, m), 2.0-1.75 (2H, m); Anal. Calcd for C14H24N4O5: C, 51.21; H, 7.37; N, 17.06. Found: C, 50.2; H, 7.3; N, 16.1

Workup

  1. concentrationconcentrated
  2. additiondiluted with CH2Cl2 (100 ml)
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9544008b82954974bca90eb9fed00b10
Source dataset
uspto-grants-2012_02
Patent number
US08119631B2

Reaction notes

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