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

HRID 537380ノート

反応式

HRID 537380 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-54465fac42764137936b7e1dbd6c6527
出典データセット
uspto-grants-2014_10
特許番号
US08859812B2

反応ノート

読み込み中…