1-Hydroxybenzotriazole → (2S)-N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide

HRID 1092477

반응식

HRID 1092477 반응식
[C:1]1([C@H:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.CC[N+](CCCN(C)C)=C=N.[CH2:34]([N:41]1[CH2:45][C@H:44]2[C@H:46]([NH2:49])[CH2:47][CH2:48][C@H:43]2[CH2:42]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[CH2:34]([N:41]1[CH2:45][C@H:44]2[C@H:46]([NH:49][C:8](=[O:10])[C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:11][CH3:12])[CH2:47][CH2:48][C@H:43]2[CH2:42]1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 785329(S)-2-Phenylbutyric acidHCID 218833923-(Dimethylamino)propyl-ethyl-(iminomethylidene)azaniumHCID 25918977(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

생성물 1

HCID 54673710(2S)-N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(S)-2-Phenylbutanoic acid (41.7 mg, 0.254 mmol), 1-hydroxybenzotriazole (38.9 mg, 0.254 mmol), and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (0.045 mL, 0.254 mmol) were combined in dichloromethane (1 mL). The reaction was stirred at room temperature for 10 minutes, and then (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine (50 mg, 0.231 mmol) from Step E was added in 0.5 mL of dichloromethane. The reaction was stirred at room temperature for 20 hours, and then quenched with 0.5 mL of water. The organic layer was separated. The crude material was chromatographed using a silica gel cartridge (Analogix®, Burlington, Wis., RS-4) eluting with 1-10% methanol(ammonia)/dichloromethane to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.47 (d, J=7.0, 1H), 7.59 (m, 2H), 7.42 (d, J=7.1, 2H), 7.34 (dd, J=7.6, 16.5, 4H), 7.25 (dt, J=5.0, 10.1, 2H), 4.45-4.29 (m, 1H), 3.62-3.51 (m, 2H), 3.44 (d, J=13.2, 1H), 2.85 (dd, J=2.7, 9.0, 1H), 2.58-2.50 (m, 1H), 2.50-2.42 (m, 2H), 2.40-2.31 (m, 1H), 2.31-2.22 (m, 2H), 1.97 (dq, J=6.1, 12.1, 1H), 1.85 (td, J=6.9, 13.6, 1H), 1.74 (dt, J=6.4, 14.3, 1H), 1.46 (dt, J=7.1, 19.2, 1H), 1.31 (dt, J=6.2, 20.5, 1H), 0.96 (dd, J=5.5, 9.1, 3H); MS (ESI+) m/z 363 (M+H)+.

후처리

  1. stirringThe reaction was stirred at room temperature for 20 hours
  2. customquenched with 0.5 mL of water
  3. customThe organic layer was separated
  4. customThe crude material was chromatographed
  5. washeluting with 1-10% methanol(ammonia)/dichloromethane

출처 및 근거

ORD 기록
ord-710f827f90094aaa9df9eb66d8007e17
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129417B2

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