3-Furanol, tetrahydro- → HCID 22291107, compound

HRID 1369541Notes

Reaction equation

HRID 1369541 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:36])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:25]=2)=[CH:18][C:17]=1[NH:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1.O[CH:48]1[CH2:52][CH2:51][O:50][CH2:49]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:36])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:25]=2)=[CH:18][C:17]=1[NH:37][C:38](=[O:46])[C:39]1[CH:40]=[CH:41][C:42]([O:45][CH:48]2[CH2:52][CH2:51][O:50][CH2:49]2)=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 99603-Furanol, tetrahydro-HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22291116HCID 22291116, compound

Product 1

HCID 22291107HCID 22291107, compoundYield 298.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Di-isopropyl azodicarboxylate (0.21 ml) was added to a stirred mixture of N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-4-hydroxybenzamide (0.15 g), 3-hydroxytetrahydrofuran (0.31 g), triphenyl phosphine (0.275 g) and methylene chloride (5 ml) which had been cooled to 5° C. The resultant mixture was stirred at ambient temperature for 18 hours. The mixture was poured onto a pre-wetted (methylene chloride) ion-exchange column (isolute SCX 5 g column from International Sorbent Technology Limited) and eluted in turn with methylene chloride (40 ml), with methylene chloride (40 ml) containing 20% methanol and with methylene chloride containing 20% methanol and 3% of a saturated aqueous ammonium hydroxide solution. The product so obtained was further purified by column chromatography on silica using a 4:1 mixture of ethyl acetate and methanol as eluent. There was thus obtained the title compound as a solid (0.52 g); Mass Spectrum: M+H+ 502.

Workup

  1. washeluted in turn with methylene chloride (40 ml), with methylene chloride (40 ml)
  2. additioncontaining 20% methanol
  3. customThe product so obtained
  4. customwas further purified by column chromatography on silica using
  5. additiona 4:1 mixture of ethyl acetate and methanol as eluent

Sources & evidence

ORD record
ord-68b1f1453d094116898164552766fdcf
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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