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

HRID 522362

반응식

HRID 522362 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fac0f28567ba41b0ab7b91c86f3a0bfb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328138B2

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