Triethylamine → (2S,5R)-5-ethynyl-1-{N-((2S)-2-hydroxycyclopentyl)glycyl}pyrrolidine-2-carbonitrile

HRID 475396노트

반응식

HRID 475396 반응식
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4].Cl.[NH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[OH:21].C(N(CC)CC)C>C(#N)C>[C:10]([C@@H:9]1[N:5]([C:3](=[O:4])[CH2:2][NH:15][CH:16]2[CH2:20][CH2:19][CH2:18][C@@H:17]2[OH:21])[C@H:6]([C:12]#[N:13])[CH2:7][CH2:8]1)#[CH:11]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 12886906(1R,2R)-2-aminocyclopentan-1-ol hydrochlorideHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

생성물 1

HCID 10467838(2S,5R)-5-ethynyl-1-{N-((2S)-2-hydroxycyclopentyl)glycyl}pyrrolidine-2-carbonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.040 g, 0.20 mmol, Example 8D) in acetonitrile (1 mL) at room temperature was added trans-2-aminocyclopentanol hydrochloride (56 mg, 0.41 mmol) and triethylamine (0.14 ml, 1.02 mmol). The reaction mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 3% methanol:dichloromethane to provide the titled compound. MS (ESI) m/z 262 (M+H)+; 1H NMR (MeOH) 4.79 (m, 1H), 4.17-4.40 (m, 3H), 3.18 (m, 1H), 2.48 (m, 4H); 2.00-2.30 (m, 4H), 1.80 (m, 2H), 1.66 (2H, m).

후처리

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography with 3% methanol

출처 및 근거

ORD 기록
ord-fa922999d72748149515b90e118775b7
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637546B2

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