1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-(t-Butoxycarbonylamino)-n-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]cyclohexylcarboxamide

HRID 1057743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057743
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C:19]1[S:20][C:21]([S:24][CH2:25][C:26]2[O:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:29][N:30]=2)=[CH:22][N:23]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(Cl)Cl.O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15]([NH:18][C:19]2[S:20][C:21]([S:24][CH2:25][C:26]3[O:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:29][N:30]=3)=[CH:22][N:23]=2)=[O:17])[CH2:13][CH2:14]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acidHCID 110654845-(((5-(tert-Butyl)oxazol-2-yl)methyl)thio)thiazol-2-amine

Produkt 1

HCID 186216364-(t-Butoxycarbonylamino)-n-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]cyclohexylcarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5 g of crude 4-(t-butoxycarbonylamino)cyclohexane carboxylic acid and 3.50 g (13 mmol) of 2-amino-5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]thiazole in 13 mL of N,N-dimethylformamide and 36 mL of methylene chloride was added 5.0 g (26 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at room temperature. The reaction mixture was stirred overnight and diluted with 100 mL of water. The aqueous layer was separated and extracted with two-150 mL portions of ethyl acetate. The combined organic phases were dried (sodium sulfate) then filtered through a pad of silica gel. The filtrate was concentrated in vacuo to afford an orange solid. The crude material was recrystallized (95% ethanol) to give 4-(t-butoxycarbonylamino)-N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]cyclohexylcarboxamide as a yellow solid. The mother liquors were also concentrated in vacuo to give additional 4-(t-butoxycarbonylamino)-N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]cyclohexylcarboxamide as a brown solid.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted with two-150 mL portions of ethyl acetate
  3. dry with materialThe combined organic phases were dried (sodium sulfate)
  4. filtrationthen filtered through a pad of silica gel
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford an orange solid
  7. customThe crude material was recrystallized (95% ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-9385dc3268f74d909f32ee4cbd31e9fd
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515004B1

Notizen zur Reaktion

Wird geladen…