Ethanol → HCID 18512057, compound

HRID 1370911Notes

Reaction equation

HRID 1370911 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15].[CH:29]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:30]=1.C(O)C>O1CCCC1>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:29][CH3:30])=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 11776TriphenylphosphineHCID 18512160N-(2,4-difluorobenzyl)-N-(4-hydroxybenzyl)-2-methyl-3-nitroaniline

Product 1

HCID 18512057HCID 18512057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 33A(39 mg, 0.1 mmole) and di-t-butylazo dicarboxylate (35 mg, 0.15 mmole) in tetrahydrofuran (1.5 ml) were added to PPh3 on resin (70 mg, 0.3 mmole: loading 3 mmole/g) followed by ethanol (5.7 mg, 0.125 mmole) in 50 microliter tetrahydrofuran. Reaction mixture was shaken at room temperature overnight. Filtered off and solvent removed. Solaris 530 organic synthesis system from PE Biosystems was used to do this reaction. The residue purified by HPLC (CH3CN:0.1 TFA in H2O) on a YMC ODS guardpak column.

Workup

  1. customReaction mixture
  2. filtrationFiltered off
  3. customsolvent removed
  4. customthis reaction
  5. customThe residue purified by HPLC (CH3CN:0.1 TFA in H2O) on a YMC ODS guardpak column

Sources & evidence

ORD record
ord-95409d0f241747c9adac37d9b4ecc499
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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