Sodium Chloride → HCID 10026366, Verbindung

HRID 2294739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294739
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:18])[CH:13](C)[C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][O:21][C:22](=[O:34])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[NH2:24].[CH3:35]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[Cl-].[Na+]>C(#N)C>[CH3:20][O:21][C:22](=[O:34])[C@H:23]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[NH:24][C:14](=[O:16])[CH2:13][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:18])[CH3:35]

Komponenten

7

Edukt 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14557400HCID 14557400, VerbindungHCID 69612215(S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

Produkt 1

HCID 10026366HCID 10026366, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 1.12 g (4.47 mmol) of N-[(benzyloxy)carbonyl]-2,3-dimethyl-β-alanine (EPA 0230266), 1.1 g (4.47 mmol) of 3-(p-methoxyphenyl)-L-alanine methyl ester hydrochloride, 1.7 g (4.47 mmol) of HBTU and 1.25 ml (8.94 mmol) of triethylamine in 40 ml of acetonitrile is stirred at room temperature for 4 hours. After the addition of 50 ml of saturated sodium chloride solution the mixture is extracted 3 times with 50 ml of ethyl acetate each time. The combined organic phases are washed in sequence with 2N hydrochloric acid, water, 50% sodium hydrogen carbonate solution and water, dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue is chromatographed on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent. N-[3-[1-(Benzyloxy)formamido]-3-methylbutyryl]-3-(p-methoxyphenyl)-L-alanine methyl ester is obtained as a colourless oil; MS: 443 (M+H)+.

Aufarbeitung

  1. extractionis extracted 3 times with 50 ml of ethyl acetate each time
  2. washThe combined organic phases are washed in sequence with 2N hydrochloric acid, water, 50% sodium hydrogen carbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customFor purification
  6. customthe residue is chromatographed on silica gel using
  7. additiona 95:5 mixture of methylene chloride and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-1a6cf864d3654add99271edae4558e29
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688946

Notizen zur Reaktion

Wird geladen…