Sodium borohydride → Methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methyl}-L-leucinate

HRID 1620901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620901
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:9][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.BrC1C=CC(C(C2C=CC(S(C)(=O)=O)=CC=2)=O)=CC=1.[BH4-].[Na+]>C(O)(=O)C.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=2)[NH:9][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 21262853(4-Bromophenyl)(4-(methylsulfonyl)phenyl)methanoneHCID 86590539methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methylene}leucinate

Produkt 1

HCID 67298353Methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methyl}-L-leucinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

To a solution of a 1:1 mixture of methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methylene}leucinate and (4-bromophenyl)[4-(methylsulfonyl)phenyl]methanone from step 1 (185 mg, −0.2 mmol) in acetic acid/methanol (1:3, 4 mL) was added sodium borohydride (˜400 mg) by portions every 30 min over 2 days (addition was stopped during the night) using a solid addition funnel. The reaction mixture was partitioned between EtOAc and water, the organic layer was dried over Na2SO4 and concentrated. The resulting mixture was purified by chromatography using EtOAc and hexane as eluant. Methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methyl}-L-leucinate was obtained as a colorless gum and (4-bromophenyl) [4-(methylsulfonyl)phenyl]methanol was obtained as a white solid.

Aufarbeitung

  1. additionaddition
  2. additiona solid addition funnel
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-599b193bac044ff08be53eeeed962032
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772336B2

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