Diisopropyl diazene-1,2-dicarboxylate → ethyl(S)-N,N'-bis(isopropoxycarbonyl)-2-cyano-2-hydrazino-2-phenylacetate

HRID 1441950

Reaction equation

HRID 1441950 reaction equation
[C:1]([CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[N:15]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[N:16][C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18]>C1(C)C=CC=CC=1>[CH:20]([O:19][C:17]([N:16]([C@:3]([C:1]#[N:2])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[NH:15][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[O:18])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 95298Ethyl phenylcyanoacetate

Product 1

HCID 68544089ethyl(S)-N,N'-bis(isopropoxycarbonyl)-2-cyano-2-hydrazino-2-phenylacetateYield 105.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 2-cyano-2-phenylacetate (23.0 mg, 0.11 mmol) and (R,R)-trans-1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(N,N-dimethylamino)cyclohexyl]thiourea (4.1 mg, 0.01 mmol) in toluene (1 mL) was added diisopropyl azodicarboxylate (21.5 μL, 0.10 mmol) at −78° C. After stirring for 15 min, the reaction mixture was concentrated. The residue was purified by silica gel column (hexane/ethyl acetate=3/1) to give the title compound (41.4 mg, yield: 100%, optical purity: 76% ee). Colorless amorphous

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by silica gel column (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-352dd41fe2c9444ca99904f7c45ddb45
Source dataset
uspto-grants-2010_02
Patent number
US07655817B2

Linked notes

Loading…