(R)-benzyl 3-(4-butoxy-4-oxobutanamido)-4-(3'-chlorobiphenyl-4-yl)butanoate → HCID 59607872, 화합물

HRID 1945008노트

반응식

HRID 1945008 반응식
[CH2:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][C:9]([NH:11][C@H:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)=[CH:27][CH:26]=1)[CH2:13][C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:10])[CH2:2][CH2:3][CH3:4]>CCOC(C)=O.[Pd]>[CH2:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][C:9]([NH:11][C@H:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)=[CH:27][CH:26]=1)[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 1

HCID 59607868(R)-benzyl 3-(4-butoxy-4-oxobutanamido)-4-(3'-chlorobiphenyl-4-yl)butanoate

생성물 1

HCID 59607872HCID 59607872, 화합물수율 60.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of (R)-benzyl 3-(4-butoxy-4-oxobutanamido)-4-(3′-chlorobiphenyl-4-yl)butanoate (178.9 mg, 0.334 mmol) and Pd/C (71.0 mg, 0.033 mmol) in EtOAc (3 ml) is allowed to stir under hydrogen at room temperature for 1.5 hours. The reaction mixture is filtered, and concentrated to give crude. The resulting residue is purified by preparative HPLC using a gradient of 20% MeCN/water (0.1% TFA) to 100% MeCN to give (R)-3-(4-butoxy-4-oxobutanamido)-4-(3′-chlorobiphenyl-4-yl)butanoic acid (90.7 mg) as a white solid; HPLC retention time=1.27 minutes (condition B); MS (m+1)=446.24; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.91 (t, J=7.5 Hz, 3H) 1.31-1.40 (m, 2H) 1.55-1.62 (m, 2H) 2.43-2.47 (m, 2H) 2.52-2.69 (m, 4H) 2.93 (A of ABX, Jab=3.7 Hz, Jax=7.7 Hz, 1H) 3.00 (B of ABX, Jab=13.7 Hz, Jbx=6.8 Hz, 1H) 4.07 (t, J=6.7 Hz, 2H) 4.49-4.57 (m, 1H) 6.31 (br d, J=8.6 Hz, 1H) 7.26-7.37 (m, 4H) 7.43-7.46 (m, 1H) 7.49-7.52 (m, 2H) 7.55 (br t, J=1.8 Hz, 1H).

후처리

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. customto give crude
  4. customThe resulting residue is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-e8d7465e0f954e3f83ab808f45ecb585
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394853B2

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