Acetic Acid → {2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}acetic acid ethyl ester

HRID 1509866노트

반응식

HRID 1509866 반응식
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([O:9][C:10](=[O:26])[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][NH2:25])=[CH:18][CH:17]=1)([CH3:8])([CH3:7])[CH3:6].C([BH3-])#N.[Na+].O1CC[CH2:33][CH2:32]1>O>[CH2:32]([O:3][C:1](=[O:4])[CH2:2][NH:25][CH2:24][CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:10]([O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[O:26])=[CH:21][CH:20]=1)[CH3:33]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 588097964-[4-(2-Aminoethoxy)phenyl]-butylcarbamic acid tert-butyl ester

생성물 1

HCID 58809798{2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}acetic acid ethyl ester수율 38%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Dimethylacetone dicarboxylate (1.43 mL, 9.69 mmol) and glacial acetic acid (0.56 mL, 9.70 mmol) were added sequentially to a solution of {4-[4-(2-aminoethoxy)phenyl]-butylcarbamic acid tert-butyl ester (1) (1.0 g, 3.24 mmol) in tetrahydrofuran (20 mL). The reaction was stirred for 2 hours at ambient temperature, then cooled to −30° C. Sodium cyanoborohydride (0.61 g, 9.70 mmol) was added in three portions and the reaction slowly warmed to room temperature over 12 hours. After this time, the reaction was quenched by the addition of water (5 mL). The volatiles was then removed under vacuum to give an oil. This oil was diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organics were washed with water (3×10 mL) and then brine (3×10 mL), dried over anhydrous sodium sulfate and concentrated to give 2 (0.576 g, 38% yield) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 1.44 (s, 9H), 1.46-1.52 (m, 2H), 1.55-1.64 (m, 2H), 2.56-2.58 (m, 4H), 2.64-2.65 (m, 2H), 2.72-2.79 (m, 2H), 2.88-2.93 (m, 2H), 3.74 (d, 6H), 3.88-3.93 (m, 1H), 4.44-4.49 (m, 2H), 6.40 (br, 1H), 6.85 (d, 2H), 7.09 (d, 2H); m/z (ESI) 467.

후처리

  1. temperaturecooled to −30° C
  2. customthe reaction
  3. temperatureslowly warmed to room temperature over 12 hours
  4. customAfter this time, the reaction was quenched by the addition of water (5 mL)
  5. customThe volatiles was then removed under vacuum
  6. customto give an oil
  7. extractionextracted with ethyl acetate (3×10 mL)
  8. washThe combined organics were washed with water (3×10 mL)
  9. dry with materialbrine (3×10 mL), dried over anhydrous sodium sulfate
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dbf556f17ff24b839b75b7a030abf43c
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211895B2

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