Triethylamine → {4'-[4-(1,1-Dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenylcarbamoyl]-6-methyl-biphenyl-3-yl}-carbamic acid tert-butyl ester

HRID 1678464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678464
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:24])=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=2)[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:25]=[S:26]1(=[O:40])[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:22])[NH:39][C:36]3[CH:37]=[CH:38][C:33]([CH2:32][N:29]4[CH2:28][CH2:27][S:26](=[O:25])(=[O:40])[CH2:31][CH2:30]4)=[CH:34][CH:35]=3)=[CH:19][CH:20]=2)[C:12]([CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27796824-(4-Aminobenzyl)thiomorpholine 1,1-dioxideHCID 598223484-[5-(Tert-butoxycarbonylamino)-2-methyl-phenyl]benzoic acid

Produkt 1

HCID 59822377{4'-[4-(1,1-Dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenylcarbamoyl]-6-methyl-biphenyl-3-yl}-carbamic acid tert-butyl esterAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5′-tert-butoxycarbonylamino-2′-methyl-biphenyl-4-carboxylic acid (500 mg), 4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl) -phenylamine (367 mg), triethylamine (0.64 ml) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (869 mg) in dry DMF (20 ml) was stirred at 20 C for 118 h. The mixture was then partitioned between water and dichloromethane. The dried extracts were evaporated and the residue purified on silica gel. Elution with ethyl acetate:petrol; 1:1 removed high Rf impurities and further elution with ethyl acetate gave the title compound as a pale yellow solid (693 mg).

Aufarbeitung

  1. customThe mixture was then partitioned between water and dichloromethane
  2. customThe dried extracts were evaporated
  3. customthe residue purified on silica gel
  4. washElution with ethyl acetate
  5. wash1:1 removed high Rf impurities and further elution with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d623748c0af3409d8c06b54dc1b04502
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008303B2

Notizen zur Reaktion

Wird geladen…