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

HRID 2384050Notes

Reaction equation

HRID 2384050 reaction equation
[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]

Participants

3

Reactant 1

HCID 67506102HCID 67506102, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7732cdd0c4c341958ef7b02258f808ce
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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