Water → (2S)-cyclopentyl[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)amino]ethanoic acid

HRID 522362ノート

反応式

HRID 522362 の反応式
[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:10]([O:12]N1C(=O)CCC1=O)=O)[CH2:2][CH2:3][C:4]#[CH:5].[NH2:20][C@@H:21]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27]C1)[C:22]([OH:24])=[O:23].C(N(CC)CC)C.O>C(#N)C.C(OCC)(=O)C>[CH:25]1([C@H:21]([NH:20][C:10]([O:9][C@@H:7]2[CH2:8][C@H:6]2[CH2:1][CH2:2][CH2:3][C:4]#[CH:5])=[O:12])[C:22]([OH:24])=[O:23])[CH2:30][CH2:29][CH2:28][CH2:27]1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 736848(alphaS)-alpha-Aminocyclohexaneacetic acidHCID 895908351-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

生成物 1

HCID 89590843(2S)-cyclopentyl[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)amino]ethanoic acid収率 100.9%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the product of Step 1 (457 mg) in acetonitrile (6 ml) was added (2S)-amino(cyclohexyl)ethanoic acid (352 mg) followed by triethylamine (0.720 ml) and water (6.00 ml). The mixture was stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate and washed with HCl 1N, water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. This provided the desired product (510 mg) as an oil. LRMS (ES+) M/Z (M+H)+ 308.2.

後処理

  1. washwashed with HCl 1N, water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-fac0f28567ba41b0ab7b91c86f3a0bfb
出典データセット
uspto-grants-2016_05
特許番号
US09328138B2

反応ノート

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