Triphenylphosphine → HCID 71203345, compound

HRID 1027719Notes

Reaction equation

HRID 1027719 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[F:32][C:33]1[CH:57]=[CH:56][CH:55]=[CH:54][C:34]=1[O:35][C:36]1[N:37]=[CH:38][C:39]2[N:44]=[C:43]([C:45]3[CH:50]=[C:49]([CH3:51])[C:48]([OH:52])=[C:47]([CH3:53])[CH:46]=3)[O:42][C:40]=2[N:41]=1.O[CH:59]1[CH2:62][CH:61]([C:63]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)=[O:64])[CH2:60]1>O1CCCC1.C(N(CC)CC)C>[F:32][C:33]1[CH:57]=[CH:56][CH:55]=[CH:54][C:34]=1[O:35][C:36]1[N:37]=[CH:38][C:39]2[N:44]=[C:43]([C:45]3[CH:46]=[C:47]([CH3:53])[C:48]([O:52][CH:59]4[CH2:62][CH:61]([C:63]([O:65][CH2:66][C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)=[O:64])[CH2:60]4)=[C:49]([CH3:51])[CH:50]=3)[O:42][C:40]=2[N:41]=1

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 22934789Benzyl 3-hydroxycyclobutane-1-carboxylateHCID 1361211154-[5-(2-Fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenol

Product 1

HCID 71203345HCID 71203345, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

At 0° C., 179 mg of triphenylphosphine and 107 μl of diethyl azodicarboxylate were initially charged in 4.5 ml of tetrahydrofuran, and the mixture was stirred for 15 min. 200 mg of 4-[5-(2-fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenol, 95 μl of triethylamine and 141 mg of benzyl 3-hydroxycyclobutanecarboxylate were then added to the reaction, and the reaction was stirred under argon, initially at room temperature for 3 h. Another 179 mg of triphenylphosphine and 107 μl of diethyl azodicarboxylate were then added, and the reaction was stirred for 12 h. For work-up, the reaction was concentrated and the resulting residue was purified by flash chromatography (silica gel, heptane/ethyl acetate). This gave 216 mg (70%) of the title compound.

Workup

  1. stirringthe reaction was stirred under argon, initially at room temperature for 3 h
  2. stirringthe reaction was stirred for 12 h
  3. concentrationFor work-up, the reaction was concentrated
  4. customthe resulting residue was purified by flash chromatography (silica gel, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-0cef18d52440445aa4c556c937b1ecdf
Source dataset
uspto-grants-2014_05
Patent number
US08735402B2

Reaction notes

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