Semicarbazide → HCID 86599023, compound

HRID 613705Notes

Reaction equation

HRID 613705 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-e1e93887dc384d458152f788e5a73393
Source dataset
uspto-grants-1999_12
Patent number
US06008217

Reaction notes

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