Sodium Bicarbonate → HCID 10543338, Verbindung

HRID 1955805

Reaktionsgleichung

Reaktionsgleichung von HRID 1955805
C([O-])(O)=O.[Na+].[CH2:6]([O:13][C:14]([O:16]NC(=O)CCC(N)=O)=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:25][C@@H:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:27]([OH:29])=[O:28]>CC(C)=O.O>[C:7]1([CH2:6][O:13][C:14]([NH:25][C@@H:26]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:27]([OH:29])=[O:28])=[O:16])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 1501866(2S)-2-amino-2-(4-methoxyphenyl)acetic acidHCID 21865880N-(benzyloxycarbonyloxy)succinamide

Produkt 1

HCID 10543338HCID 10543338, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18366337Propan-2-one--water (1/1)Lösungsmittel

Versuchsvorschrift

A suspension of NaHCO3 (184 mg, 2.2 mmol), commercially available N-(benzyloxycarbonyloxy)succinamide (548 mg, 2.2 mmol) and (S)-α-amino-4-methoxybenzeneacetic acid (360 mg, 2 mmol), synthesis described in U.S. Pat. No. 3,517,023, in 1:1 acetone/H2O was stirred for 18 hours at 20° C. After partial concentration and extraction with CH2Cl2, the pH was adjusted to 1.5 and the solution extracted with EtOAc (3×). The EtOAc extracts were washed with brine, dried over MgSO4 and concentrated to yield (S)-α-[N-[(phenylmethoxy)carbonyl]amino]-4-methoxybenzeneacetic acid. A solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (608 mg, 3.2 mmol), hydroxybenztriazole (643 mg, 4.76 mmol) and (S)-α-[N-(phenylmethoxy)carbonyl]amino-4-methoxybenzeneacetic acid (1 g, 3.17 mmol) in CH2Cl2 (10 mL) was stirred one hour at 0° C. whereupon N-methylmorpholine (0.7 mL, 6.4 mmol) and t-butylamine (0.5 mL, 4.8 mmol) were added and the reaction stirred at 20° C. for 18 hours. The reaction was diluted with EtOAc, washed with H2O, aq. NaHCO3, brine, dried over MgSO4, and concentrated. Pure (S)-N-(1,1-dimethylethyl)-α-[N-[(phenylmethoxy)carbonyl]amino]-4-methoxybenzeneacetamide was obtained after chromatography on silica gel using 35% EtOAc/hexane as eluant. Hydrogenation of (S)-N-(1,1-dimethylethyl)-α-[N-[(phenylmethoxy)carbonyl]amino]-4-methoxybenzeneacetamide over 10% Pd(OH)2 /C at 1 atom of H2 in 1:1 MeOH/EtOAc generated the title compound which required no further purification following filtration and concentration.

Aufarbeitung

  1. concentrationAfter partial concentration and extraction with CH2Cl2
  2. extractionthe solution extracted with EtOAc (3×)
  3. washThe EtOAc extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9b60ac16e3b84408babf9837bd87dfb3
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05776983

Verknüpfte Notizen

Wird geladen…