HCID 59608104, compound → HCID 178461715, compound

HRID 2384032Notes

Reaction equation

HRID 2384032 reaction equation
C([O:8][C:9](=[O:42])[C@H:10]([CH3:41])[CH2:11][C@H:12]([NH:26][C:27]([C:29]1[N:33](CC2C=CC=CC=2)[N:32]=[N:31][N:30]=1)=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.C(OC(=O)[C@H](C)C[C@H](NC(C1N=NN(CC2C=CC=CC=2)N=1)=O)CC1C=CC(C2C=CC=CC=2)=CC=1)C1C=CC=CC=1>CO.[Pd]>[C:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:18]=[CH:19][C:14]([CH2:13][C@@H:12]([NH:26][C:27]([C:29]2[NH:33][N:32]=[N:31][N:30]=2)=[O:28])[CH2:11][C@@H:10]([CH3:41])[C:9]([OH:42])=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 59608104HCID 59608104, compoundHCID 59608156HCID 59608156, compound

Product 1

HCID 178461715HCID 178461715, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2R,4S)-4-[(1-benzyl-1H-tetrazole-5-carbonyl)-amino]-5-biphenyl-4-yl-2-methyl-pentanoic acid benzyl ester and (2R,4S)-4-[(2-benzyl-2H-tetrazole-5-carbonyl)-amino]-5-biphenyl-4-yl-2-methyl-pentanoic acid benzyl ester (126 mg, 0.225 mmol) in MeOH is hydrogenated with 10% Pd/C for 6 h. The reaction mixture is concentrated and purified by reverse phase HPLC to give (2R,4S)-5-biphenyl-4-yl-2-methyl-4-[(1H-tetrazole-5-carbonyl)-amino]-pentanoic acid. HPLC Retention time 1.16 minutes (condition D); MS 380.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (d, J=7.20 Hz, 3H), 1.63-1.73 (m, 1H), 1.86-1.95 (m, 1H), 2.40-2.50 (m, 1H), 2.80-2.95 (m, 2H), 4.22-4.34 (m, 1H), 7.29-7.35 (m, 1H), 7.43 (dd, J=7.83, 7.83 Hz, 2H), 7.55 (d, J=10.23 Hz, 2H), 7.61-7.64 (2H, m), 9.16 (d, J=9.09 Hz, 1H), 12.03, (s, 1H).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-94875979d753455b9f3745986293a0ff
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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