Sodium Bicarbonate → HCID 21712328, compound

HRID 650841Notes

Reaction equation

HRID 650841 reaction equation
[CH2:1]([N:8]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])[NH:9]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.ClCCl>[CH2:1]([N:8]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])[NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 21712326HCID 21712326, compound

Product 1

HCID 21712328HCID 21712328, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of of 2-benzyl-1-tert-butoxycarbonyl-4-ethylsemicarbazide (2.8 g, 9.6 mmol) in 50% trifluoroacetic acid in dichloromethane (10 ml) was stirred for 10 min at room temperature. Then saturated sodium bicarbonate was added until pH>7 and the aqueous layer was extracted with dichloromethane (2×10 ml) and the combined organic layers were dried (magnesium sulfate) and concentrated in vacuo. The obtained oil was chromatographed on silica (100 g) with ethyl acetate as eluent to give 1.7 g of 2-benzyl-4-ethylsemicarbazide.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane (2×10 ml)
  2. dry with materialthe combined organic layers were dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe obtained oil was chromatographed on silica (100 g) with ethyl acetate as eluent

Sources & evidence

ORD record
ord-06e3f15576a048b9b38f9578fc6d26a8
Source dataset
uspto-grants-2001_08
Patent number
US06274584B1

Reaction notes

Loading…