Acetic Acid → HCID 178474961, 화합물

HRID 1909360노트

반응식

HRID 1909360 반응식
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C@H:19]4[CH2:24][CH2:23][C@H:22]([NH2:25])[CH2:21][CH2:20]4)[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[C:35](O)(=[O:37])[CH3:36].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C@H:19]4[CH2:20][CH2:21][C@H:22]([NH:25][C:35](=[O:37])[CH3:36])[CH2:23][CH2:24]4)[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178479251HCID 178479251, 화합물2회

생성물 1

HCID 178474961HCID 178474961, 화합물수율 61.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of Trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperidin-1-yl)-ethyl]-cyclohexylamine hydrochloride (intermediate A) (50 mg, 0.136 mmol) in DMF (0.8 ml) was added N,N-diisopropylethylamine (62 mg, 0.0833 ml, 0.477 mmol), acetic acid (9.82 mg, 9.35 μl, 0.164 mmol) and TBTU (52.4 mg, 0.164 mmol). The mixture was allowed to stir at room temperature for 4 h and poured into ice/water (0.5 ml) The crude reaction mixture was concentrated in vacuo. The reaction mixture was solved with sat NaHCO3 (1×10 mL). and extracted with dichloromethane (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 0% to 20% MeOH in dichloromethane) to yield the title compound as an white solid (31 mg, 61%), MS (ISP) m/z=373.5 [(M+H)+].

후처리

  1. customreaction mixture
  2. concentrationwas concentrated in vacuo
  3. extractionand extracted with dichloromethane (3×20 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 10 g, 0% to 20% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-db0705dc3b4244ec9a5d750fd97f161a
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598357B2

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