Acetic Acid → N-(3-Cyano-6-{[1-(hydroxymethyl)-2,2-dimethylpropyl]amino}-4,5,6,7-tetrahydro-1-benzothien-2-yl)-2-ethylbutanamide

HRID 917349

Reaktionsgleichung

Reaktionsgleichung von HRID 917349
[C:1]([C:3]1[C:7]2[CH2:8][CH2:9][C:10](=O)[CH2:11][C:6]=2[S:5][C:4]=1[NH:13][C:14](=[O:20])[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])#[N:2].[NH2:21][CH:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:23][OH:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl.C([O-])(O)=O.[Na+]>[C:1]([C:3]1[C:7]2[CH2:8][CH2:9][CH:10]([NH:21][CH:22]([CH2:23][OH:24])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:11][C:6]=2[S:5][C:4]=1[NH:13][C:14](=[O:20])[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])#[N:2]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 41492122-Amino-3,3-dimethylbutan-1-olHCID 5049666Sodium triacetoxyborohydrideHCID 58962835N-(3-Cyano-6-oxo-4,5,6,7-tetrahydro-1-benzothien-2-yl)-2-ethylbutanamide

Produkt 1

HCID 58962825N-(3-Cyano-6-{[1-(hydroxymethyl)-2,2-dimethylpropyl]amino}-4,5,6,7-tetrahydro-1-benzothien-2-yl)-2-ethylbutanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of the intermediate isolated in Example 9, Step C, in 40 mL of dichloromethane was added 0.452 g (3.90 mmol) of 2-amino-3,3-dimethylbutan-1-ol, followed by 1.24 g (5.9 mmol) of sodium triacetoxyborohydride and 0.468 mL (7.80 mmol) of acetic acid. After 16 h at ambient temperature the reaction was diluted with an equal volume of saturated aqueous NaHCO3. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification by preparative reversed phase HPLC afforded the title compound (TFA salt).

Aufarbeitung

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. concentrationconcentrated in vacuo
  3. customPurification by preparative reversed phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-caf7821ad0d54ab6abf035ce69687821
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273876B2

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