1,2-Dichloroethane → (R)-benzyl 2-(tert-butoxycarbonylamino)-2-(1-methylcyclohexyl)acetate

HRID 537380노트

반응식

HRID 537380 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[CH2:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)CCl>CN(C)C1C=CN=CC=1.CCOCC>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([O:12][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 6344DichloromethaneHCID 67052824(2R)-2-(tert-butoxycarbonylamino)-2-(1-methylcyclohexyl)acetic acid

생성물 1

HCID 86678253(R)-benzyl 2-(tert-butoxycarbonylamino)-2-(1-methylcyclohexyl)acetate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매

실험 절차

A 2-dram vial containing a small stirbar was charged with (R)-2-(tert-butoxycarbonylamino)-2-(1-methylcyclohexyl)acetic acid (10d) (11 mg, 0.04 mmol), CH2Cl2 (1 mL), 4-dimethylaminopyridine (2 mg, 0.02 mmol, 0.5 equiv), benzyl alcohol (20 μL, 0.2 mmol, 5 equiv), and EDC (20 mg, 0.1 mmol, 2.5 equiv). The solution was stirred at room temperature for 3 h, and then diluted with 10 mL Et2O. The mixture was washed with water (2×10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (7:1 hexanes/Et2O) and analyzed by chiral HPLC analysis: (AS-H, 1 mL/min, 2% IPA/hexanes, 210 nm): tR(minor)=6.84 min, tR(major)=8.13 min.

후처리

  1. additionA 2-dram vial containing a small stirbar
  2. washThe mixture was washed with water (2×10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (7:1 hexanes/Et2O)
  6. custom=6.84 min
  7. customtR(major)=8.13 min.

출처 및 근거

ORD 기록
ord-54465fac42764137936b7e1dbd6c6527
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859812B2

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