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

HRID 1642714ノート

反応式

HRID 1642714 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-61db150878444065aacdef3ad304ac5d
出典データセット
uspto-grants-2012_02
特許番号
US08119664B2

反応ノート

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