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 2105895노트

반응식

HRID 2105895 반응식
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]

참가 물질

6

반응물 4

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

생성물 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]carbamate수율 45%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-269b16f100d84dc3b02fc1a91f3a7d1a
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579464B2

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