Triphenylphosphine → HCID 21904891, compound

HRID 1247314Notes

Reaction equation

HRID 1247314 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][C:9](=[O:21])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[F:20])[O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].[F:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]O)=[CH:27][CH:26]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:21])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:30][CH2:29][C:28]3[CH:32]=[CH:33][C:25]([F:24])=[CH:26][CH:27]=3)=[CH:15][C:14]=2[F:20])[O:11][CH3:12])=[CH:22][CH:23]=1)#[N:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 820684-Fluorophenethyl AlcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21905330HCID 21905330, compound

Product 1

HCID 21904891HCID 21904891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to example 22.1, (RS)-N-(4-cyano-benzyl)-2-(2-fluoro-4-hydroxy-phenyl)-2-methoxy-acetamide (example 70.4) was reacted with 4-fluorophenethyl alcohol, diethyl azodicarboxylate and triphenyl-phosphine in THF to give (RS)-N-(4-cyano-benzyl)-2-{2-fluoro-4-[2-(4-fluoro-phenyl)-ethoxy]-phenyl}-2-methoxy-acetamide. Colorless oil. MS 437.3 ([M+H]+)

Sources & evidence

ORD record
ord-b4fbec2e0a2d472c9f3bf284d1ba3190
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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