Acetic Acid → (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxylic acid

HRID 239093

Reaktionsgleichung

Reaktionsgleichung von HRID 239093
[NH2:1][C@@:2]1([C:22]#[N:23])[C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:6][C@@H:5]2[C@H:3]1[C@@:4]2([F:21])[C:18](N)=[O:19].C(O)(=[O:26])C.Cl>O>[NH2:1][C@@:2]1([C:22]#[N:23])[C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:6][C@@H:5]2[C@H:3]1[C@@:4]2([F:21])[C:18]([OH:26])=[O:19]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 53236629(1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide

Produkt 1

HCID 68227684(1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture containing 22.5 mg of (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide (6a), 0.1 mL of acetic acid, 0.1 mL of water, and 0.2 mL of concentrated hydrochloric acid was stirred for 6 hrs approximately under heating at 75° C. (external temperature). The reaction mixture was concentrated under reduced pressure to obtain 24.6 mg of (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxylic acid (6f) as a light brown solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-59beab20337e40e9a15d84ebd334399f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642777B2

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