3-(3'-Hydroxyphenyl)propionic acid → HCID 22627082, compound

HRID 278160Notes

Reaction equation

HRID 278160 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:17])#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[OH:49][C:50]1[CH:51]=[C:52]([CH2:56][CH2:57][C:58](O)=[O:59])[CH:53]=[CH:54][CH:55]=1>C1COCC1>[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][O:14][C:58](=[O:59])[CH2:57][CH2:56][C:52]3[CH:53]=[CH:54][CH:55]=[C:50]([OH:49])[CH:51]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:17])#[N:2]

Participants

6

Reactant 4

HCID 913-(3'-Hydroxyphenyl)propionic acidHCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 185360621-(4-Cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole

Product 1

HCID 22627082HCID 22627082, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the alcohol from Step F (79.7 mg, 0.345 mmol) and triphenylphosphine (90.0 mg, 0.345 mmol) in 0.5 mL of THF was added a solution of diethylazodicarboxylate (0.054 mL, 0.345 mmol) and 3-(3-hydroxyphenyl)propionic acid (57 mg, 0.34 mmol) in 0.5 mL of THF. After 10 minutes, HPLC analysis indicated 60% conversion. Additional triphenylphosphine (45 mg, 0.17 mmol) and diethylazodicarboxylate (0.027 mL, 0.17 mmol) were added, and the reaction was stirred for 10 more minutes. The solution was concentrated in vacuo, then purified by silica gel chromatography (3% MeOH/CH2Cl2) to provide the desired product as a white foam.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified by silica gel chromatography (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5d8292145f4044e4aecf70603cfd4ddc
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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