Dicyclohexylcarbodiimide → 8-{[(Benzyloxy)carbonyl]amino}-1,2,3,4-tetrahydronaphthalen-2-yl (2r)-methoxy(phenyl)acetate

HRID 1672542ノート

反応式

HRID 1672542 の反応式
[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[CH3:23][O:24][C@H:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26](O)=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:23][O:24][C@H:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26]([O:1][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[C:9]([NH:12][C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:22])[CH:8]=[CH:7][CH:6]=2)[CH2:11]1)=[O:27]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 2724294(R)-(-)-alpha-methoxyphenylacetic acidHCID 66696602Benzyl 7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-ylcarbamate

生成物 1

HCID 908939218-{[(Benzyloxy)carbonyl]amino}-1,2,3,4-tetrahydronaphthalen-2-yl (2r)-methoxy(phenyl)acetate収率 89.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of Example 24B (1.03 g, 3.46 mmol), (R)-2-methoxy-2-phenylacetic acid (0.633 g, 3.81 mmol), 1,3-dicyclohexylcarbodiimide (1.14 g, 5.54 mmol), and 4-dimethylaminopyridine (0.846 g, 6.93 mmol) in dichloromethane (35 mL) was stirred at ambient temperature for 18 hr. The reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous NH4Cl solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was placed on a silica gel column and eluted with 30% ethyl acetate/hexanes to afford 1.38 g (89% yield) of the title compound as a colorless syrup. MS (ESI+) m/z 446 (M+H)+, 463 (M+NH4).

後処理

  1. washwashed with saturated aqueous NH4Cl solution, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washeluted with 30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-30bcf3f86cde46caadba104865280780
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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