1,2-Dichloroethane → HCID 178494981, Verbindung

HRID 2355499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2355499
[C:1]([NH:3][C:4]([NH:6][C@@H:7]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:8][N:9]([CH3:19])[C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])=S)#[N:2].Cl[C:28]1[CH:29]=[C:30]([C@:34]([C@@H:42]2[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]2)([OH:41])[CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:31]=[CH:32][CH:33]=1.C(Cl)CCl>CN(C=O)C.CCOCC>[C:1]([N:3]=[C:4]([N:44]1[CH2:45][CH2:46][CH2:47][C@@H:42]([C@:34]([OH:41])([C:30]2[CH:29]=[CH:28][CH:33]=[CH:32][CH:31]=2)[CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH2:43]1)[NH:6][C@@H:7]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:8][N:9]([CH3:19])[C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])#[N:2]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 59382814(S)-1-(3-chlorophenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-olHCID 866530841-cyano-3-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)thiourea

Produkt 1

HCID 178494981HCID 178494981, VerbindungAusbeute 38,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-cyano-3-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)thiourea (230 mg, 0.58 mmol) and (S)-1-(3-chlorophenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (180 mg, 0.58 mmol) in DMF (5 mL) was added EDC (0.17 g, 0.87 mmol). The mixture was stirred for 16 h at rt, diluted with ether (175 mL) and washed with 5% aq HCl (2×50 mL) and brine (50 mL). The combined aqueous washes were back extracted with ether. The combined ether extracts were concentrated to afford crude product (290 mg). The mixture was purified by prep HPLC to afford (3R)—N′-cyano-N—((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carboxamidine (145 mg, 37%).

Aufarbeitung

  1. washwashed with 5% aq HCl (2×50 mL) and brine (50 mL)
  2. extractionThe combined aqueous washes were back extracted with ether
  3. concentrationThe combined ether extracts were concentrated
  4. customto afford crude product (290 mg)
  5. customThe mixture was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1af1db235072473ab5036d5dd3c23478
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754737B2

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