Diisopropylethylamine → Methyl 2-[(4-{2-[[2-(4-chlorophenyl)ethyl](heptyl)-amino]-2-oxoethyl}benzyl)oxy]benzoate

HRID 2112063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2112063
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]([C:22]1[CH:39]=[CH:38][CH:37]=[CH:36][C:23]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([OH:35])=O)=[CH:28][CH:27]=1)=[O:21].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:33](=[O:35])[CH2:32][C:29]2[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:23]3[CH:36]=[CH:37][CH:38]=[CH:39][C:22]=3[C:20]([O:19][CH3:18])=[O:21])=[CH:31][CH:30]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 43130216N-[2-(4-chlorophenyl)ethyl]-N-heptylamineHCID 68872997(4-{[2-(Methoxycarbonyl)phenoxy]methyl}phenyl)acetic acid

Produkt 1

HCID 68870508Methyl 2-[(4-{2-[[2-(4-chlorophenyl)ethyl](heptyl)-amino]-2-oxoethyl}benzyl)oxy]benzoateAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-[2-(4-Chlorophenyl)ethyl]-N-heptylamine (0.127 g, 0.500 mmol) was dissolved in DMF (10 ml), (4-{[2-(methoxycarbonyl)phenoxy]methyl}phenyl)acetic acid (0.150 g, 0.500 mmol) was added and the mixture was cooled to 0° C. N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (0.176 g, 0.549 mmol) and N-ethyl-N,N-diisopropylamine (0.136 g, 1.049 mmol) was added. The solution was stirred overnight at room temperature. EtOAc (20 ml) was added and the organic phase was washed with two portions of Na2CO3 (2×20 ml, aq). The organic layer was dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (started with isocratic acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions were pooled and the acetonitrile was removed by evaporation EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4) and the solvent was removed by evaporation to give 0.224 g of methyl 2-[(4-{2-[[2-(4-chlorophenyl)ethyl](heptyl)-amino]-2-oxoethyl}benzyl)oxy]benzoate (yield 83.7%).

Aufarbeitung

  1. washthe organic phase was washed with two portions of Na2CO3 (2×20 ml, aq)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe crude was purified by preparative HPLC (
  5. concentrationthe acetonitrile concentration
  6. temperaturewas increased to 100%
  7. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)
  8. additionThe product containing fractions
  9. customthe acetonitrile was removed by evaporation EtOAc (10 ml)
  10. additionwas added
  11. washthe organic phase was washed with two portions of brine
  12. dry with materialdried (MgSO4)
  13. customthe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-901e5537e92d469795a900ce1ae7a6eb
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521461B2

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