4-Methylmorpholine → (S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1678502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678502
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][C:18]([F:21])([F:20])[F:19])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[C:22]([O:26][C:27]([N:29]1[CH2:32][CH2:31][C@H:30]1[C:33]([OH:35])=O)=[O:28])([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=N[C:46]2C=CC=C[C:45]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[C:22]([O:26][C:27]([N:29]1[CH2:32][CH2:31][C@H:30]1[C:33](=[O:35])[NH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:45][CH3:46])=[O:15])=[CH:12][CH:13]=2)[C:5]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:4][CH:3]=1)=[O:28])([CH3:23])([CH3:24])[CH3:25]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acidHCID 673729305'-Amino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid

Produkt 1

HCID 67371803(S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl esterAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5′-amino-2′-trifluoromethoxy-biphenyl-4-carboxylic acid (150 mg), (S)-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester (93 mg), HBTU (262 mg) and N-methyl morpholine (0.14 ml) in dry DMF (3 ml) was stirred at room temp for 18 h. The mixture was then partitioned between water and DCM. The dried organic layer was evaporated and the residue purified on silica gel. Elution with ethyl acetate:petrol 1:1 gave a pale orange oil (185 mg).

Aufarbeitung

  1. customThe mixture was then partitioned between water and DCM
  2. customThe dried organic layer was evaporated
  3. customthe residue purified on silica gel
  4. washElution with ethyl acetate:petrol 1:1

Quellen und Nachweise

ORD-Eintrag
ord-65f520f383b24dc4a74c1939a07159ab
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008303B2

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