Triphenylphosphine → benzyl N-[4-[[[2-[2,6-difluoro-4-(2-morpholin-4-ylethoxy)phenyl]-2-ethoxyacetyl]amino]methyl]benzenecarboximidoyl]carbamate

HRID 1247369Notes

Reaction equation

HRID 1247369 reaction equation
[CH2:1]([O:8][C:9](=[O:36])[NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21](=[O:35])[CH:22]([C:26]2[C:31]([F:32])=[CH:30][C:29]([OH:33])=[CH:28][C:27]=2[F:34])[O:23][CH2:24][CH3:25])=[CH:15][CH:14]=1)=[NH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:36])[NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21](=[O:35])[CH:22]([C:26]2[C:31]([F:32])=[CH:30][C:29]([O:33][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[CH:28][C:27]=2[F:34])[O:23][CH2:24][CH3:25])=[CH:15][CH:14]=1)=[NH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 97268Di-tert-butyl azodicarboxylateHCID 140474529benzyl N-[4-[[[2-(2,6-difluoro-4-hydroxyphenyl)-2-ethoxyacetyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 140474528benzyl N-[4-[[[2-[2,6-difluoro-4-(2-morpholin-4-ylethoxy)phenyl]-2-ethoxyacetyl]amino]methyl]benzenecarboximidoyl]carbamateYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (RS)-[(4-{[2-(2,6-difluoro-4-hydroxy-phenyl)-2-ethoxy-acetylamino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester (100 mg), N-(2-hydroxyethyl)morpholine (29 mg) and polymer bound triphenylphosphine (˜3 mmol/g, 167 mg) in CH2Cl2 (2 ml) was added di-tert-butyl azodicarboxylate (93 mg) before shaking 22 h at rt. After filtration of the polymer the solvent was evaporated and the residue was purified by HPLC to obtain 28 mg of (23%) (RS)-{[4-({2-[2,6-difluoro-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-ethoxy-acetylamino}-methyl)-phenyl]-imino-methyl}-carbamic acid benzyl ester.

Workup

  1. filtrationAfter filtration of the polymer the solvent
  2. customwas evaporated
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-d2ca78ba227a439fb64a3c656ba786fc
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

Loading…