Dichloromethane → (2R,3R,4S,5R,6E)-7-(2-bromophenyl)-3,4,5-trihydroxy-2-methoxy-N-[(3S)-5-methyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide

HRID 1670440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670440
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C@H:10]([C@@H:12]1[O:16][C:15](=[O:17])[C@H:14]([O:18][CH3:19])[C@@H:13]1[OH:20])[OH:11].Cl.[NH2:22][C@@H:23]1[C:29](=[O:30])[N:28]([CH3:31])[C:27]2[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=2[O:25][CH2:24]1.C(C(CCCC)C([O-])=O)C.[Na+].C(Cl)Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C@@H:10]([OH:11])[C@H:12]([OH:16])[C@@H:13]([OH:20])[C@@H:14]([O:18][CH3:19])[C:15]([NH:22][C@@H:23]1[C:29](=[O:30])[N:28]([CH3:31])[C:27]2[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=2[O:25][CH2:24]1)=[O:17]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 23672331Sodium 2-ethylhexanoateHCID 57617788(3R,4R,5S)-5-[(1R,2E)-3-(2-bromophenyl)-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-oneHCID 67328139(3S)-3-amino-5-methyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-4-one hydrochloride

Produkt 1

HCID 57617758(2R,3R,4S,5R,6E)-7-(2-bromophenyl)-3,4,5-trihydroxy-2-methoxy-N-[(3S)-5-methyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

90 mg of 45 (0.22 mmol), 51 mg of 6 (0.22 mmol) and 93 mg of sodium 2-ethylhexanoate (0.56 mmol) in 2.0 mL of THF are successively introduced into a 10 mL round-bottomed flask, with stirring and under an argon atmosphere. The stirring is maintained at RT for 24 h. 20 mL of CH2Cl2 are added to the reaction medium. The mixture is successively washed with 10 mL of an HCl solution (1N), 10 mL of water saturated with NaCl. The organic phase is dried over anhydrous magnesium sulphate, filtered and then evaporated to dryness. The crude product is chromatographed on a silica cartridge (9 g, eluent, AcOEt/heptane:85/15). 49 mg of expected product Ex18 (white solid) are recovered.

Aufarbeitung

  1. washThe mixture is successively washed with 10 mL of an HCl solution (1N), 10 mL of water saturated with NaCl
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product is chromatographed on a silica cartridge (9 g, eluent, AcOEt/heptane:85/15)
  6. custom49 mg of expected product Ex18 (white solid) are recovered

Quellen und Nachweise

ORD-Eintrag
ord-9db73c273f97403289f9e1923cc9d727
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994161B2

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