Chloroacetamide → N-[N2-(1(S)-carboxy-3-phenylpropyl)-N6-carbamoylmethyl-L-lysyl]-L-proline

HRID 1583933

Reaktionsgleichung

Reaktionsgleichung von HRID 1583933
[C:1]([C@@H:4]([NH:13][C@H:14]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([OH:3])=[O:2].C(N(CC)CC)C.Cl[CH2:38][C:39]([NH2:41])=[O:40]>O.C(O)C>[C:1]([C@@H:4]([NH:13][C@H:14]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:38][C:39](=[O:40])[NH2:41])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([OH:3])=[O:2]

Komponenten

6

Edukt 3

HCID 6580ChloroacetamideHCID 8471TriethylamineHCID 5362119Lisinopril

Produkt 1

HCID 86740515N-[N2-(1(S)-carboxy-3-phenylpropyl)-N6-carbamoylmethyl-L-lysyl]-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

In 4.0 ml of water there was dissolved N-[N2 -(1(S)-carboxy-3-phenylpropyl)-L-lysyl]-L-proline (406 mg, 0.0001 mole), after which triethylamine (364 mg, 0.0036 mole) was added, followed by slow, dropwise addition of a solution of 2-chloroacetamide (140.3 mg, 0.0015 mole) in 6.0 ml of ethanol. The reaction mixture was stirred at room temperature for 15 minutes, followed by refluxing with stirring for 15 hours. Thin layer chromatography indicated a nearly complete reaction, and the refluxing was continued for 2 more hours. The reaction mixture is allowed to cool and then concentrated under vacuum, flushed with benzene 3 times, then further concentrated under vacuum. The crude product was purified on a 2.5×240 cm LH-20 chromatographic column using a methanol system. Product-rich fractions were evaporated to dryness and freeze-dried to give N-[N2 -(1(S)-carboxy-3-phenylpropyl)-N6 -carbamoylmethyl-L-lysyl]-L-proline.

Aufarbeitung

  1. temperatureby refluxing
  2. stirringwith stirring for 15 hours
  3. customa nearly complete reaction
  4. temperatureto cool
  5. concentrationconcentrated under vacuum
  6. customflushed with benzene 3 times
  7. concentrationfurther concentrated under vacuum
  8. customThe crude product was purified on a 2.5×240 cm LH-20 chromatographic column
  9. customProduct-rich fractions were evaporated to dryness
  10. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-981bdc6958c24b4fb9d464ca4d155b40
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04555503

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