Triethylamine → benzyl (1S,3R)-3-(4-chlorobutanamido)cyclohexylcarbamate

HRID 74972

Reaktionsgleichung

Reaktionsgleichung von HRID 74972
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1.CCN(CC)CC.[Cl:26][CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31]>C(Cl)Cl>[Cl:26][CH2:27][CH2:28][CH2:29][C:30]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1)=[O:31]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 69756715Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate2×

Produkt 1

HCID 68101865benzyl (1S,3R)-3-(4-chlorobutanamido)cyclohexylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred slurry of benzyl N-[(1S,3R)-3-aminocyclohexyl]carbamate, 18e, (0.97 g, 3.41 mmol) in CH2Cl2 (34 mL), was added Et3N (1.00 mL, 7.15 mmol), followed by 4-chlorobutanoyl chloride (0.40 mL, 3.58 mmol). After stirring at room temperature, the mixture was diluted with CH2Cl2, washed with 1N HCl (2×), 1N NaOH (2×), and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give 1.07 g of the desired product.

Aufarbeitung

  1. washwashed with 1N HCl (2×), 1N NaOH (2×), and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-33806c5de7e74f21baa2a380cd0f178b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829007B2

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