Sodium borohydride → N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl ester

HRID 1060419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060419
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:33])[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]=[O:32])=[CH:21][CH:20]=1)[NH:7][C:8](=[O:17])[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16]>CO>[CH3:3][O:4][C:5](=[O:33])[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][OH:32])=[CH:21][CH:20]=1)[NH:7][C:8](=[O:17])[C:9]1[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=1[Cl:15]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 54369932N-(2,6-Dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester

Produkt 1

HCID 53694008N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl esterAusbeute 103,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

NaBH4 (21 mg) was added to a solution of N-(2,6-dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester (0.23 g) in MeOH (5 mL) and the mixture was stirred at room temperature for 3 h. The reaction was quenched with acetone and the mixture was evaporated. The residue was partitioned between EtOAc and water. The EtOAc layer was dried (MgSO4) and evaporated to yield N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl ester (0.24 g). ESMS: m/z 480 ([M+Na]+).

Aufarbeitung

  1. customThe reaction was quenched with acetone
  2. customthe mixture was evaporated
  3. customThe residue was partitioned between EtOAc and water
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5f9cb3978ed34f00ac7fd0e9581da922
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521666B1

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