Acetyl chloride → (R)-tert-butyl 8-(acetoxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazine-2(1H)-carboxylate

HRID 1482982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1482982
[OH:1][CH2:2][C:3]1[C:4]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:5][C:6]2[N:10]3[CH2:11][CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:14]([CH:15]([CH3:17])[CH3:16])[C:9]3=[N:8][C:7]=2[CH:25]=1.CCN(CC)CC.[C:37](Cl)([CH3:39])=[O:38].CCOC(C)=O>C(Cl)Cl>[C:37]([O:1][CH2:2][C:3]1[C:4]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:5][C:6]2[N:10]3[CH2:11][CH2:12][N:13]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[C@H:14]([CH:15]([CH3:16])[CH3:17])[C:9]3=[N:8][C:7]=2[CH:25]=1)(=[O:38])[CH3:39]

Komponenten

6

Edukt 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 89815566(R)-tert-butyl 8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazine-2(1H)-carboxylate

Produkt 1

HCID 89815908(R)-tert-butyl 8-(acetoxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazine-2(1H)-carboxylateAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 50 mL round-bottomed flask containing (R)-tert-butyl 8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazine-2(1H)-carboxylate (236 mg, 0.558 mmol) in CH2Cl2 (5 mL) was added Et3N (169 mg, 1.67 mmol) and AcCl (87 mg, 1.12 mmol) under N2. The mixture was stirred at rt for 10 min. The reaction was quenched with water (20 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with water (25 mL) and brine, and then dried over anhydrous Na2SO4. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with PE:EtOAc 8:1-4:1 to give (R)-tert-butyl 8-(acetoxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazine-2(1H)-carboxylate (210 mg, 81.1% yield) as a yellow solid.

Aufarbeitung

  1. customThe reaction was quenched with water (20 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic layers were washed with water (25 mL) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel eluting with PE

Quellen und Nachweise

ORD-Eintrag
ord-828a6ef8d1fe4144b298db218515bfe0
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416135B2

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