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

HRID 1672542노트

반응식

HRID 1672542 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-30bcf3f86cde46caadba104865280780
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998993B2

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