1,2-Dichloroethane → methyl (S)-alpha-[(S)-alpha-[(tert-butylsulphonyl)methyl]hydrocinnamamido]imidazole-4-propionate

HRID 2294722

Reaktionsgleichung

Reaktionsgleichung von HRID 2294722
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=O)(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:22][O:23][C:24](=[O:33])[C@H:25]([CH2:27][C:28]1[N:32]=[CH:31][NH:30][CH:29]=1)[NH2:26].C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C)C=O>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([NH:26][C@@H:25]([CH2:27][C:28]1[N:32]=[CH:31][NH:30][CH:29]=1)[C:24]([O:23][CH3:22])=[O:33])=[O:12])(=[O:6])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 9860623(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamic acidHCID 178419105HCID 178419105, Verbindung

Produkt 1

HCID 178501410methyl (S)-alpha-[(S)-alpha-[(tert-butylsulphonyl)methyl]hydrocinnamamido]imidazole-4-propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5.7 (20 mmol) of (S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamic acid (EPA 0236734) 4.85 g (20 mmol) of L-histidine methyl ester dihydrochloride, 10.3 ml (81.7 mmol) of N-ethylmorpholine and 2.98 g (20 mmol) of HOBT in 85 ml of dimethylformamide is treated portionwise under argon at 0°-2° with 4.23 g (22 mmol) of EDC and subsequently stirred at room temperature overnight. Thereafter, the solvent is evaporated in a high vacuum, the residue is taken up in 100 ml of ethyl acetate and washed in sequence three times with 10 ml of 2N sodium bicarbonate solution, twice with 10 ml of saturated sodium chloride solution, twice with 10 ml of saturated ammonium chloride solution and twice with 5 ml of saturated sodium chloride solution. The aqueous phases are extracted three times with 20 ml of ethyl acetate and the pooled organic phases are dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude product obtained (9.4 g) is chromatographed on 300 g of silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent. There are obtained 8.6 g of methyl (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]imidazole-4-propionate as a colourless foam; MS: 436 (M+H)+.

Aufarbeitung

  1. customThereafter, the solvent is evaporated in a high vacuum
  2. washwashed in sequence three times with 10 ml of 2N sodium bicarbonate solution, twice with 10 ml of saturated sodium chloride solution, twice with 10 ml of saturated ammonium chloride solution and twice with 5 ml of saturated sodium chloride solution
  3. extractionThe aqueous phases are extracted three times with 20 ml of ethyl acetate
  4. dry with materialthe pooled organic phases are dried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customFor purification
  7. customthe crude product obtained (9.4 g)
  8. customis chromatographed on 300 g of silica gel using
  9. additiona 95:5 mixture of methylene chloride and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-2e2506739fbc4e0db5814e838df3554c
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688946

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