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 1670440ノート

反応式

HRID 1670440 の反応式
[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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9db73c273f97403289f9e1923cc9d727
出典データセット
uspto-grants-2011_08
特許番号
US07994161B2

反応ノート

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