Diazomethane → methyl(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoate

HRID 1180421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180421
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[N+](=[CH2:26])=[N-]>CO.C(OCC)C.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([O:13][CH3:26])=[O:12])=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 9550DiazomethaneHCID 69470808(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid

Produkt 1

HCID 69469636methyl(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid from step 2 example 1, (2.5 g, 6.6 mmol) in methanol (25 mL) at 0° C. was added portionwise diazomethane in diethyl ether until the yellow color persisted. A few drops of acetic acid were then added to quench the excess diazomethane. The colorless solution was concentrated and then the volatiles were coevaporated twice with n-heptane. The oil was pumped on to remove the last traces of solvent.

Aufarbeitung

  1. customto quench the excess diazomethane
  2. concentrationThe colorless solution was concentrated
  3. customto remove the last traces of solvent

Quellen und Nachweise

ORD-Eintrag
ord-2ab83d1ffcf44afc93354abb2b6faf93
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279478B2

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