1,2-Dichloroethane → HCID 59511757, Verbindung

HRID 1157451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157451
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C@@H:14]([CH3:17])[CH2:15][OH:16])=[CH:8][C:4]=1[C:5]([OH:7])=O.[NH2:18][CH2:19][C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C@@H:14]([CH3:17])[CH2:15][OH:16])=[CH:8][C:4]=1[C:5]([NH:18][CH2:19][C:20](=[O:21])[NH:22][CH:23]([CH3:25])[CH3:24])=[O:7]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5338492-Amino-N-isopropylacetamideHCID 68524390HCID 68524390, Verbindung

Produkt 1

HCID 59511757HCID 59511757, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-5-[(S)-(+)-3-hydroxy-2-methylpropoxy]benzoic acid hydrochloride (200 mg, 0.76 mmol), 2-amino-N-isopropylacetamide*HCl (INTERMEDIATE I.1) (105 mg, 0.70 mmol) and triethylamine (0.23 mL, 1.68 mmol) in DMF (5 mL) was stirred at room temperature for 5 min. EDC (176 mg, 0.92 mmol) and HOBt (124 mg, 0.92 mmol) were added and stirring continued at room temperature for 16 h. The mixture was partitioned between ethyl acetate and sat. NaHCO3 (aq.) and the aqueous extracted with additional ethyl acetate. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude 2-amino-5-[(S)-(+)-3-hydroxy-2-methylpropoxy]-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE VIII.1) was used directly in the next reaction.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at room temperature for 16 h
  3. customThe mixture was partitioned between ethyl acetate and sat. NaHCO3 (aq.)
  4. extractionthe aqueous extracted with additional ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude 2-amino-5-[(S)-(+)-3-hydroxy-2-methylpropoxy]-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE VIII.1) was used directly in the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-349a2737e5714664a84460541d331871
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807686B2

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