4-Methylmorpholine → (R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester

HRID 234211

Reaktionsgleichung

Reaktionsgleichung von HRID 234211
[C:1]([O:20][C@@H](C)C(O)=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:27][O:28][C:29](=[O:34])[C@H:30]([CH2:32][SH:33])[NH2:31].Cl.CN(C)[CH2:38][CH2:39][CH2:40]N=C=NCC.CN1CC[O:51][CH2:50]C1>C(#N)C>[CH3:27][O:28][C:29](=[O:34])[C@@H:30]([NH:31][C:50](=[O:51])[C@@H:39]([CH3:38])[CH2:40][O:20][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:32][SH:33]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733208L-Cysteine, methyl ester, hydrochlorideHCID 54161083(S)-2-trityloxypropionic acid

Produkt 1

HCID 54008528(R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl esterAusbeute 16,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a suspension of 9.97 g of (S)-2-trityloxy-propionic acid, 5.60 g of L-cysteine methyl ester hydrochloride and 6.6 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride in 50 ml acetonitrile was added over 10 min a solution of 6.9 g of 4-methyl-morpholine in 50 ml of acetonitrile. The mixture was stirred at room temperature for 3 h and then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent to yield 2.30 g of (R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester as amorphous solid. 1H-NMR (250 MHz,DMSO-d6): δ0.88(d,J=10 Hz,3H); 2.42(t,J=15 Hz, 1H); 2.78 (dd,J=10 Hz and 15 Hz,2H); 3.66(s,3H); 4.01(q,J=10 Hz, 1H); 4.20-4.30(m, 1H); 7.25-7.50(m, 16H); 7.82(d,J=16 Hz,1H) ppm.

Aufarbeitung

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e0c84cc91f1d439183e58be7b2c7be11
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594135

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