Water → [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] N-[(7S)-5-[(4-methoxyphenyl)methyl]-6-oxo-7H-benzo[d][1]benzazepin-7-yl]carbamate

HRID 2105895ノート

反応式

HRID 2105895 の反応式
O.[NH2:2][CH:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=2[C:5]2[CH:24]=[CH:25][CH:26]=[CH:27][C:4]1=2.C([O-])([O-])=O.[K+].[K+].Cl[C:35]([O:37][CH:38]1[CH:43]([CH:44]([CH3:46])[CH3:45])[CH2:42][CH2:41][C@@H:40]([CH3:47])[CH2:39]1)=[O:36]>C1COCC1>[CH:44]([C@@H:43]1[CH2:42][CH2:41][C@@H:40]([CH3:47])[CH2:39][C@H:38]1[O:37][C:35](=[O:36])[NH:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=2[C:5]2[CH:24]=[CH:25][CH:26]=[CH:27][C:4]1=2)([CH3:45])[CH3:46]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20577931(-)-(r)-Menthyl chloroformateHCID 210725617-Amino-5-(4-methoxybenzyl)-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one

生成物 1

HCID 44516082[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] N-[(7S)-5-[(4-methoxyphenyl)methyl]-6-oxo-7H-benzo[d][1]benzazepin-7-yl]carbamate収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Water (40 mL) was added to a yellow solution of 7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one (7.45 g) in THF (40 mL) at room temperature forming a light yellow suspension. To this suspension were added K2CO3 (5.53 g) in one portion and, after 15 minutes of stirring, (−)-(1R)-menthyl chloroformate (4.96 g) was added within 30 minutes. The dropping funnel was washed with THF. The emulsion was stirred for 105 minutes at room temperature. Heptane (486 mL) was added within 40 minutes and, after 60 more minutes of stirring, the precipitate was filtered off, washed with heptane, water, and then heptane in that order and dried under vacuum at 55° C. to afford [(S)-5-(4-methoxy-benzyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-carbamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (4.75 g, 45%), d.e=99.8:0.2 (HPLC), as a white powder.

後処理

  1. customforming a light yellow suspension
  2. washThe dropping funnel was washed with THF
  3. stirringThe emulsion was stirred for 105 minutes at room temperature
  4. additionHeptane (486 mL) was added within 40 minutes
  5. stirringafter 60 more minutes of stirring
  6. filtrationthe precipitate was filtered off
  7. washwashed with heptane, water
  8. dry with materialheptane in that order and dried under vacuum at 55° C.

出典と根拠

ORDレコード
ord-269b16f100d84dc3b02fc1a91f3a7d1a
出典データセット
uspto-grants-2009_08
特許番号
US07579464B2

反応ノート

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