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

HRID 1593992
ノート
印刷プレビュー

反応式

HRID 1593992 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bc423b0b15aa42a5945bed9994fd58e4
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07300934B2

反応ノート

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