Hydrochloric Acid → 3-((2S,3R)-4-azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione

HRID 253600노트

반응식

HRID 253600 반응식
[N:1]([CH2:4][C@@H:5]([OH:23])[C@@H:6]([NH:14][C:15]1[C:16](=O)[C:17](=[O:21])[C:18]=1[O:19]C)[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[N+:2]=[N-:3].Cl.[CH3:25][O:26][CH2:27][CH2:28][CH2:29][O:30][CH:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH:32]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]1.CCN(CC)CC>C(#N)C>[N:1]([CH2:4][C@@H:5]([OH:23])[C@@H:6]([NH:14][C:15]1[C:18](=[O:19])[C:17](=[O:21])[C:16]=1[N:34]1[CH2:35][CH2:36][CH2:37][CH:32]([CH:31]([O:30][CH2:29][CH2:28][CH2:27][O:26][CH3:25])[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:33]1)[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)=[N+:2]=[N-:3]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 574196003-((3-Methoxypropoxy)(phenyl)methyl)piperidineHCID 577865243-((2S,3R)-4-Azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-methoxycyclobut-3-ene-1,2-dione

생성물 1

HCID 577864683-((2S,3R)-4-azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione수율 67.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3-((2S,3R)-4-Azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-methoxycyclobut-3-ene-1,2-dione (35 mg, 0.11 mmol), the HCl salt of 3-((3-methoxypropoxy)(phenyl)methyl)piperidine (48 mg, 0.16 mmol), and Et3N (100 μL, 0.7 mmol) were dissolved in acetonitrile (1 mL). The reaction was allowed to stir at rt overnight. The solvent was evaporated and the product was isolated by preparative HPLC to give 3-((2S,3R)-4-azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione (41 mg). MS m/z 554 (M+H+).

후처리

  1. customThe solvent was evaporated
  2. customthe product was isolated by preparative HPLC

출처 및 근거

ORD 기록
ord-e87d67c52ae944b3badee6ca2306d210
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872028B2

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