1,2-Dichloroethane → HCID 57888800, 화합물

HRID 1016145노트

반응식

HRID 1016145 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([N:24]([CH3:32])[C@H:25]([CH:29]([CH3:31])[CH3:30])[C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][N:11]([C:26](=[O:27])[C@H:25]([N:24]([CH3:32])[C:22](=[O:23])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:29]([CH3:31])[CH3:30])[CH2:10][C:9]2([CH3:14])[CH3:15])=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 7018800Boc-N-methyl-D-ValineHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

생성물 1

HCID 57888800HCID 57888800, 화합물수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (100 mg, 0.417 mmol), (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (116 mg, 0.501 mmol), HOBT (77 mg, 0.501 mmol), EDC (96 mg, 0.501 mmol) and triethylamine (0.116 mL, 0.834 mmol) were mixed in methylene chloride (3 mL) at 25° C. with stirring. The reaction was stirred for 20 hours then washed with sat'd sodium bicarbonate. The methylene chloride layer was dried over sodium sulfate and concentrated in vacuo to give a white glass which was purified over silica gel (9:1 to 3:1 to 1:1 Hexanes/EtOAc) to obtain tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl(methyl)carbamate (190 mg, 0.417 mmol, 100% yield) as a white glass. MS found: (M+H)+=453.15.

후처리

  1. stirringThe reaction was stirred for 20 hours
  2. washthen washed with sat'd sodium bicarbonate
  3. dry with materialThe methylene chloride layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a white glass which
  6. customwas purified over silica gel (9:1 to 3:1 to 1:1 Hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-38f3d1c819a44e8b9b5ba22fae4d6b1f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985861B2

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