Isopropanol → HCID 68005660, compound

HRID 74450Notes

Reaction equation

HRID 74450 reaction equation
N(C(OC(C)C)=O)=NC(O[CH:6]([CH3:8])[CH3:7])=O.[CH2:15]([O:17][C:18]([C:20]1[N:21]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:22]2[C:27]([CH:28]=1)=[CH:26][C:25]([OH:29])=[CH:24][CH:23]=2)=[O:19])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(O)C>O1CCCC1>[CH2:15]([O:17][C:18]([C:20]1[N:21]([S:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=2)(=[O:32])=[O:31])[C:22]2[C:27]([CH:28]=1)=[CH:26][C:25]([O:29][CH:6]([CH3:8])[CH3:7])=[CH:24][CH:23]=2)=[O:19])[CH3:16]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 680059685-hydroxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 68005660HCID 68005660, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.15 ml, 0.75 mmol) was added to an anhydrous tetrahydrofuran (THF) solution (2.5 ml) of 5-hydroxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (175 mg, 0.48 mmol), triphenylphosphine (197 mg, 0.75 mmol), and 2-propanol (0.2 ml, 4.0 mmol), and stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 5-isopropoxy-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester as a colorless gum-like material (166.7 mg, 87%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e226669acfbd414396ded5cb12224da8
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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