Sodium Hydroxide → (R)-3-(biphenyl-4-ylmethyl)-4-(2-carboxyethylamino)-4-oxobutanoic acid

HRID 881824노트

반응식

HRID 881824 반응식
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([C:13]([NH:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[O:14])[CH2:9][C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO>[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@@H:8]([C:13]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])[CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1

참가 물질

5

반응물 2

HCID 14798Sodium Hydroxide2회HCID 59607696(R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid2회

생성물 1

HCID 59607892(R)-3-(biphenyl-4-ylmethyl)-4-(2-carboxyethylamino)-4-oxobutanoic acid수율 76.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid (Intermediate 5: 22.1 mg, 0.060 mmol) in THF (0.6 mL) and methanol (0.1 mL), aqueous 1M NaOH (0.12 mL, 0.12 mmol) is added at room temperature. After stirring for 3 hours, additional aqueous 1M NaOH (0.12 mL, 0.12 mmol) is added. The reaction mixture is allowed to stir for 30 minutes and quenched with 0.5 mL of aqueous 1M HCl and 0.5 mL of brine. The mixture is extracted twice with ethyl acetate, and the organic layer is concentrated under reduced pressure to give (R)-3-(biphenyl-4-ylmethyl)-4-(2-carboxyethylamino)-4-oxobutanoic acid (16.4 mg). HPLC retention time=1.04 minutes (condition A); MS (m+1)=356.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.13-2.31 (m, 3 H) 2.59-2.65 (m, 1 H) 2.81-2.90 (m, 2 H) 3.12-3.27 (m, 2 H) 7.26 (d, 2 H, J=8 Hz) 7.34 (t, 1 H, J=7.4 Hz) 7.45 (t, 2 H, J=7.7 Hz) 7.57 (d, 2 H, J=8.1 Hz) 7.63-7.65.

후처리

  1. stirringto stir for 30 minutes
  2. customquenched with 0.5 mL of aqueous 1M HCl and 0.5 mL of brine
  3. extractionThe mixture is extracted twice with ethyl acetate
  4. concentrationthe organic layer is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-51310a7fff8a4ddda8f1375fa3f9dc3a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993631B2

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