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Citric Acid → HCID 178523110, 화합물

HRID 2406806
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HRID 2406806 반응식
[F:1][C:2]([F:28])([F:27])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][O:17][C:18]2[C:19]([C:24]([NH2:26])=[O:25])=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:10])[CH2:5][CH2:4]1.[H-].[Na+].I[CH2:32][C:33]1([OH:39])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN1CCCC1=O>[OH:39][C:33]1([CH2:32][NH:26][C:24](=[O:25])[C:19]2[C:18]([O:17][CH2:16][C@H:12]3[CH2:13][CH2:14][CH2:15][N:11]3[C:9]([C@H:6]3[CH2:7][CH2:8][C@H:3]([C:2]([F:1])([F:27])[F:28])[CH2:4][CH2:5]3)=[O:10])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 669618924-(iodomethyl)tetrahydro-2H-pyran-4-olHCID 178513798HCID 178513798, 화합물

생성물 1

HCID 178523110HCID 178523110, 화합물수율 53.3%

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

실험 절차

To a solution of 3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinamide (105 mg, 0.263 mmol, EXAMPLE 75 Step 1) in 1-Methyl-2-pyrrolidone (5 mL) was added sodium hydride (60% oil dispersant, 16 mg, 0.394 mmol) at ambient temperature. After being stirred at room temperature for 1 h, 4-(iodomethyl)tetrahydro-2H-pyran-4-ol (76 mg, 0.315 mmol, EXAMPLE 77 Step 1) was added to the mixture. The mixture was heated at 70° C. and stirred for 3 days. After cooling to room temperature, aq. citric acid was added to the mixture. The mixture was extracted with ethyl acetate twice and washed successively with aq. sodium thiosulfate, aq. sodium bicarbonate, and brine. The extracts were combined and dried over sodium sulfate and concentrated in vacuo to afford 72 mg of crude oil. The residual oil was purified by preparative HPLC purification.

후처리

  1. temperatureThe mixture was heated at 70° C.
  2. stirringstirred for 3 days
  3. temperatureAfter cooling to room temperature
  4. extractionThe mixture was extracted with ethyl acetate twice
  5. washwashed successively with aq. sodium thiosulfate, aq. sodium bicarbonate, and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5fe5a1e8d6484fbab689735947a64370
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809380B2

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