Triphenylphosphine → HCID 70161140, compound

HRID 991393Notes

Reaction equation

HRID 991393 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:59]1[S:63][CH:62]([CH2:64]O)[CH2:61][CH2:60]1)[CH2:57][CH3:58]>C1COCC1>[CH2:56]([CH:59]1[S:63][CH:62]([CH2:64][O:55][C:52]2[CH:51]=[CH:50][C:49]([C:46]3[N:47]=[CH:48][C:43]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:44][N:45]=3)=[CH:54][CH:53]=2)[CH2:61][CH2:60]1)[CH2:57][CH3:58]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18413608HCID 18413608, compoundHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 70161140HCID 70161140, 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-undecyl-pyrimidin-2-yl)phenol and 5-propyl-tetrahydrothiophen-2-yl-methanol (prepared by LiAIH4 reduction of methyl 5-propyl-tetrahydrothiophene-2-carboxylate). 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. The compounds (I-13) and (I-14) can be obtained in a similar manner.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customPurification
  3. customby chromatography (silica gel, dichloromethane) and recrystallization
  4. customaffords the target compound
  5. customThe compounds (I-13) and (I-14) can be obtained in a similar manner

Sources & evidence

ORD record
ord-38b6250366084954a4449fcc97b37266
Source dataset
uspto-grants-2002_10
Patent number
US06465060B1

Reaction notes

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