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

HRID 1469628ノート

反応式

HRID 1469628 の反応式
[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]

参加物

3

反応物 1

HCID 67506102HCID 67506102、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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); 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.05-1.10 (m, 3 H) 1.10-1.16 (m, 3 H) 1.69-1.79 (m, 1 H) 1.88 (ddd, J=13.89, 9.98, 3.92 Hz, 1 H) 2.77-2.87 (m, 1 H) 2.87-2.96 (m, 1 H) 3.91-4.05 (m, J=10.72, 7.14, 7.14, 3.66, 3.66 Hz, 2 H) 4.24 (br. s., 1 H) 6.85-6.85 (m, 0 H) 7.30 (d, J=8.34 Hz, 2 H) 7.37-7.42 (m, 1 H) 7.46 (t, J=7.83 Hz, 1 H) 7.56-7.64 (m, 3 H) 7.68 (t, J=1.77 Hz, 1 H) 9.18 (br. s., 1 H).

後処理

  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

出典と根拠

ORDレコード
ord-934ae7874bae4656a99275459e62e724
出典データセット
uspto-grants-2015_04
特許番号
US09006249B2

反応ノート

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