Water → HCID 11302325, 화합물

HRID 1173003

반응식

HRID 1173003 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[C:14]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>ClC(Cl)C.ClCCl>[C:14]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:15]=[CH:16][C:17]([CH2:20][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]3[CH2:10][C@H:9]3[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=2)=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

생성물 1

HCID 11302325HCID 11302325, 화합물수율 61%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

A suspension of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.28 g, 1.58 mmol) and 4-biphenylcarbaldehyde (0.32 g, 1.74 mmol) in dichloroethane (20 mL) were heated to reflux until a clear solution formed. The solution was cooled to RT then NaB(OAc)3H (0.50 g, 2.37 mmol) was added and stirred for 2 h. Water (50 mL) and dichloromethane (50 mL) were added and the organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude material was purified on silica gel eluting with an increasing gradient from hexanes to 40% ethyl acetate/hexanes to give the title compound as a white solid (0.33 g, 61%). 1H NMR (400 MHz, DMSO) δ 12.15 (s, 1H), 7.65-7.59 (m, 4H), 7.46-7.41 (m, 4H), 7.34 (t, J=7.3 Hz, 1H), 6.84 (d, J=8.6 Hz, 2H), 6.51 (d, J=8.4 Hz, 2H), 6.22 (s, 1H), 4.29 (s, 2H), 2.23-2.18 (m, 1H), 1.62-1.57 (m, 1H), 1.32-1.28 (m, 1H), 1.21-1.16 (m, 1H). ES-MS m/z 344.2 (MH+).

후처리

  1. temperaturewere heated
  2. temperatureto reflux until a clear solution
  3. customformed
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified on silica gel eluting with an increasing gradient from hexanes to 40% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-d2f63c0d95044922a6311666e062e434
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834013B2

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