Hydrogen Bromide → HCID 178462028, Verbindung

HRID 1252525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252525
C(OC([NH:11][C@@H:12]([CH2:33][C:34](=[O:53])[NH:35]C(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)[C:13]([NH:15][C@H:16]([C@@H:20]([NH:22][C@H:23]([C:30]([OH:32])=[O:31])[CH2:24][C:25]1[N:26]=[CH:27][NH:28][CH:29]=1)[CH3:21])[C:17]([OH:19])=[O:18])=[O:14])=O)C1C=CC=CC=1.Br.C(OCC)(=O)C>C(O)(=O)C>[NH2:11][C@@H:12]([CH2:33][C:34](=[O:53])[NH2:35])[C:13]([NH:15][C@H:16]([C@@H:20]([NH:22][C@H:23]([C:30]([OH:32])=[O:31])[CH2:24][C:25]1[N:26]=[CH:27][NH:28][CH:29]=1)[CH3:21])[C:17]([OH:19])=[O:18])=[O:14]

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 178491198HCID 178491198, Verbindung

Produkt 1

HCID 178462028HCID 178462028, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of (2R,3S)-2-[[(2S)-2-benzyloxycarbonylamino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]butyric acid (635 mg) and 30% hydrogen bromide in acetic acid (5 ml) was stirred for 2 hours at room temperature and the mixture was poured into a mixture of ice-water (20 ml) and ethyl acetate (20 ml). The aqueous phase was separated and subjected to a column of Dowex 50W x 8 (H+, 20 ml). The column was washed with water and the elution was carried out with 2.8% aqueous ammonia. The object fractions were collected and evaporated in vacuo. The residue was dissolved in water (50 ml) and lyophilized to give (2R,3S)-2-[[(2S)-2-amino-3-carbamoylpropionyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]butyric acid (190 mg) as a white powder.

Aufarbeitung

  1. customThe aqueous phase was separated
  2. washThe column was washed with water
  3. washthe elution
  4. customThe object fractions were collected
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in water (50 ml)

Quellen und Nachweise

ORD-Eintrag
ord-7a1d5cf4936846a399f2249577730946
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743614

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