Diethyl azodicarboxylate → HCID 54186787, compound

HRID 369548Notes

Reaction equation

HRID 369548 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:31][C@H:32](OC1C=CC(C2C=CC=CC=2C([O-])=O)=CC=1[N+]([O-])=O)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>>[CH3:31][C@H:32]([O:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:22]([N+:28]([O-:30])=[O:29])[CH:23]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 3

HCID 5462977Diethyl azodicarboxylateHCID 13685267HCID 13685267, compoundHCID 86755961HCID 86755961, compound

Product 1

HCID 54186787HCID 54186787, compoundYield 76%

Procedure

DEAD (777 mg, 4.46 mmol), TPP (1.171 g, 4.46 mmol), R-2-octanol (511 mg, 3.93 mmol), and compound 54 (875 mg, 3.57 mmol) were reacted according to the procedure for compound 32a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-80/20 (Hex/EtOAc). Evaporation of solvent yielded 972 mg (76%) of a light yellow oil.

Workup

  1. customThe crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-80/20 (Hex/EtOAc)
  2. customEvaporation of solvent

Sources & evidence

ORD record
ord-2d485bb25ab54f48bd989555ef170816
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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