1-Butanol → HCID 70003907, compound

HRID 1266710Notes

Reaction equation

HRID 1266710 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:14]2[CH:19]=[C:18]([O:20][CH2:21][CH3:22])[CH:17]=[C:16]([O:23][CH2:24][CH3:25])[C:15]=2[F:26])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].[CH2:27](O)[CH2:28][CH2:29][CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:27]([O:12][C:11](=[O:13])[CH:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH3:22])[CH:17]=[C:16]([O:23][CH2:24][CH3:25])[C:15]=1[F:26])[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18551841HCID 18551841, compound

Product 1

HCID 70003907HCID 70003907, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (RS)-(4-cyano-phenylamino)-(3,5-diethoxy-2-fluoro-phenyl)-acetic acid (220 mg) described in example 2.15 was dissolved in THF (3.3 ml). n-Butanol (64 mg), triphenylphosphine (179 mg) and diethylazo dicarboxylate (122 mg) were added and the mixture was stirred for 3 h at room temperature. The mixture was concentrated and the product was purified by column chromatography to give 109 mg of (RS)-(4-cyano-phenylamino)-(3,5-diethoxy-2-fluoro-phenyl)-acetic acid butyl ester as an off-white solid. MS: 414 ([M+H]+)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-8a9e7641f2e5450bbd813e4d07c6a746
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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