4-Hydroxybiphenyl → HCID 59759083, compound

HRID 914517Notes

Reaction equation

HRID 914517 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([S:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=[O:12])[S:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]1([C:41]2[CH:46]=[CH:45][C:44](O)=[CH:43][CH:42]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:35]1([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:40]=[CH:39][C:38]([O:1][CH2:2][CH2:3][C:4]2[N:5]=[C:6]([S:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=[O:12])[S:7][CH:8]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67396216HCID 67396216, compound

Product 1

HCID 59759083HCID 59759083, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-{[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid resin (0.3 g) synthesized in Example 713-1 in tetrahydrofuran (3.0 mL) were added triphenylphosphine (0.12 g) and 4-phenylphenol (0.17 g), and the mixture was left standing for 15 min. Thereto was added diisopropyl azodicarboxylate (40% toluene solution, 0.26 ml), and the mixture was stirred at room temperature for 30 min. The resin was collected by filtration from the reaction mixture, and washed three times with tetrahydrofuran. This operation was repeated three times, and the obtained resin was washed three times each with dimethylformamide, tetrahydrofuran and methanol, and vacuum dried. To the resin was added trifluoroacetic acid, and the mixture was left standing at room temperature for 4 hr. The resin was filtered off and the filtrate was concentrated by blowing nitrogen gas thereto, and purified by HPLC to give the title compound (0.012 g) as a colorless oil.

Workup

  1. waitthe mixture was left
  2. filtrationThe resin was collected by filtration from the reaction mixture
  3. washwashed three times with tetrahydrofuran
  4. washthe obtained resin was washed three times each with dimethylformamide, tetrahydrofuran and methanol, and vacuum
  5. customdried
  6. additionTo the resin was added trifluoroacetic acid
  7. waitthe mixture was left
  8. waitstanding at room temperature for 4 hr
  9. filtrationThe resin was filtered off
  10. concentrationthe filtrate was concentrated
  11. custompurified by HPLC

Sources & evidence

ORD record
ord-1ff89335f1084edd922951641d18654e
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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