HCID 67506102, 화합물 → (2R,4S)-5-(3'-Chloro-biphenyl-4-yl)-2-methyl-4-[(2H-tetrazole-5-carbonyl)-amino]-pentanoic acid ethyl ester

HRID 2384050노트

반응식

HRID 2384050 반응식
[CH2:1]([O:3][C:4](=[O:40])[C@@H:5]([CH3:39])[CH2:6][CH:7]([NH:22][C:23]([C:25]1[N:26]=[N:27][N:28](CC2C=CC(OC)=CC=2)[N:29]=1)=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:40])[C@H:5]([CH3:39])[CH2:6][C@H:7]([NH:22][C:23]([C:25]1[N:29]=[N:28][NH:27][N:26]=1)=[O:24])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:13][CH:14]=1)[CH3:2]

참가 물질

3

반응물 1

HCID 67506102HCID 67506102, 화합물

생성물 1

HCID 59608348(2R,4S)-5-(3'-Chloro-biphenyl-4-yl)-2-methyl-4-[(2H-tetrazole-5-carbonyl)-amino]-pentanoic acid ethyl ester

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

Next, a solution of (S)-5-(3′-chloro-biphenyl-4-yl)-4-{[2-(4-methoxy-benzyl)-2H-tetrazole-5-carbonyl]-amino}-2-methyl-pentanoic acid ethyl ester (212 mg, 0.377 mmol) in TFA (5 mL) is stirred at room temperature for 18 hours. The solvent is removed under reduced pressure and the residue is purified by chiral HPLC on a Chirapak IA column using heptane/ethanol (80:20) (0.1% TFA) to elute the title compound; HPLC Retention time 1.59 minutes (condition C): MS 442.2 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.05-1.10 (m, 3H) 1.10-1.16 (m, 3H) 1.69-1.79 (m, 1H) 1.88 (ddd, J=13.89, 9.98, 3.92 Hz, 1H) 2.77-2.87 (m, 1H) 2.87-2.96 (m, 1H) 3.91-4.05 (m, J=10.72, 7.14, 7.14, 3.66, 3.66 Hz, 2H) 4.24 (br. s., 1H) 6.85-6.85 (m, 0H) 7.30 (d, J=8.34 Hz, 2H) 7.37-7.42 (m, 1H) 7.46 (t, J=7.83 Hz, 1H) 7.56-7.64 (m, 3H) 7.68 (t, J=1.77 Hz, 1H) 9.18 (br. s., 1H).

후처리

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by chiral HPLC on a Chirapak IA column
  3. washto elute the title compound

출처 및 근거

ORD 기록
ord-7732cdd0c4c341958ef7b02258f808ce
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263629B2

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