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Hydrochloric Acid → [2-(1-Cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

HRID 1593992
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HRID 1593992 반응식
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:27])[NH:18][CH:19]([C:24](=O)[NH2:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>N1C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:27])[NH:18][CH:19]([C:24]#[N:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 20732578[2-(1-Carbamoyl-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

생성물 1

HCID 20732579[2-(1-Cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester수율 90%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a 0° C. solution of the amide of step 3 (13.2 g, 33.9 mmol) in 150 mL of anhydrous pyridine was added trifluoroacetic anhydride (5.50 mL, 38.9 mmol) dropwise slowly over a 3 min period. The reaction mixture was stirred for 15 min and then poured into a slurry of ice and 1N HCl solution. The mixture was extracted with 500 mL of ethyl acetate, and washed with three 400 mL portions of 1N HCl, 400 mL of water, dried over sodium sulfate, filtered and concentrated to give a crude solid. Recrystallization from ethyl acetate/hexanes gave 11.3 g of [2-(1-Cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester as a white solid. Yield: 90%, MS: 394 (M+Na+), mp=103.6-106.5° C.

후처리

  1. extractionThe mixture was extracted with 500 mL of ethyl acetate
  2. washwashed with three 400 mL portions of 1N HCl, 400 mL of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid
  7. customRecrystallization from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-bc423b0b15aa42a5945bed9994fd58e4
출처 데이터셋
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07300934B2

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