Triphenylphosphine → HCID 22134212, compound

HRID 1826558Notes

Reaction equation

HRID 1826558 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:32]([C:43]1[CH:44]=[N:45][C:46]([C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)=[N:47][CH:48]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[CH2:56]([CH:58]1[CH2:62][CH2:61][C:60]([CH2:63]O)=[CH:59]1)[CH3:57]>C1COCC1>[CH2:32]([C:43]1[CH:44]=[N:45][C:46]([C:49]2[CH:50]=[CH:51][C:52]([O:55][CH2:63][C:60]3[CH2:61][CH2:62][CH:58]([CH2:56][CH3:57])[CH:59]=3)=[CH:53][CH:54]=2)=[N:47][CH:48]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22134204HCID 22134204, compoundHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 22134212HCID 22134212, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A fully reacted mixture of equimolar amounts of diethyl azodicarboxylate and triphenylphosphine in THF is admixed with equimolar amounts of 4-(5-undecylpyrimidin-2-yl)phenol and 3-ethyl-1-cyclopenten-1-yl-methanol (prepared by LiAlH4 reduction of methyl 3-ethyl-1-cyclopentene-1-carboxylate as described by Takeda, Bull.Chem.Soc.Jpn. 50 (7), 1831 (1977)). The mixture is stirred for 24 h at room temperature and then evaporated to dryness under reduced pressure. Purification by chromatography (silica gel, dichloromethane) and recrystallization affords the target compound.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customPurification
  3. customby chromatography (silica gel, dichloromethane) and recrystallization
  4. customaffords the target compound

Sources & evidence

ORD record
ord-a5cee881299544058b43573733dab384
Source dataset
uspto-grants-2006_05
Patent number
US07052742B1

Reaction notes

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