Sodium Hydroxide → 1-Carboxymethyl-3-(S)-[(1-carboxy-2-phenylethyl)amino]perhydroazepin-2-one

HRID 1249265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1249265
[NH2:1][C@H:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:9][C:10]([OH:12])=[O:11])[C:3]1=[O:13].[OH-].[Na+].O.[C:17]1([CH2:23][C:24](=O)[C:25]([O-:27])=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na+].C([BH3-])#N.[Na+]>O>[C:10]([CH2:9][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:2]([NH:1][CH:24]([C:25]([OH:27])=[O:26])[CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:3]1=[O:13])([OH:12])=[O:11]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 13749497[(3S)-3-Amino-2-oxoazepan-1-yl]acetic acidHCID 23666336Sodium phenylpyruvate monohydrate

Produkt 1

HCID 186057891-Carboxymethyl-3-(S)-[(1-carboxy-2-phenylethyl)amino]perhydroazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Prepare an aqueous solution of 500 mg 3-(S)-amino-1-carboxymethylperhydroazepin-2-one in 5 ml water. Adjust the pH to 6 with 1N sodium hydroxide solution and add 15 ml water. React this amine with 2.24 g sodium phenylpyruvate monohydrate and 400 mg sodium cyanoborohydride as described in Example 1. Purify 370 mg of the crude product on an LH-20 column and isoalte 240 mg of 1-carboxymethyl-3-(S)-[(1-carboxy-2-phenylethyl)amino]perhydroazepin-2-one.

Aufarbeitung

  1. customPurify 370 mg of the crude product on an LH-20 column and isoalte 240 mg of 1-carboxymethyl-3-(S)-[(1-carboxy-2-phenylethyl)amino]perhydroazepin-2-one

Quellen und Nachweise

ORD-Eintrag
ord-04d478682aeb491f8ef1731bc6dead2b
Quelldatensatz
uspto-grants-1986_12
Patentnummer
US04629787

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