HCID 59608120, compound → HCID 59608192, compound

HRID 1469638Notes

Reaction equation

HRID 1469638 reaction equation
[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:19][C:20]([C:22]2[N:23]=[N:24][N:25](CC3C=CC=CC=3)[N:26]=2)=[O:21])[CH2:9][C@@H:10]([CH3:18])[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[O:12])=[CH:3][CH:2]=1>CO.CCOC(C)=O.[Pd]>[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:19][C:20]([C:22]2[N:23]=[N:24][NH:25][N:26]=2)=[O:21])[CH2:9][C@@H:10]([CH3:18])[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[O:12])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 59608120HCID 59608120, compound

Product 1

HCID 59608192HCID 59608192, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Next, A solution of 2-benzyl-2H-tetrazole-5-carboxylic acid ((1S,3R)-1-biphenyl-4-ylmethyl-4-methanesulfonylamino-3-methyl-4-oxo-butyl)-amide in MeOH/EtOAc is hydrogenated under H2 baloon by catalyst 10% Pd/C wet for 2 hours. The reaction is filtered off the catalyst and is concentrated. Reverse phase HPLC [35 to 80% ACN—H2O (0.1% TFA) over 10 min by Sunfire C18 column] provides 2H-Tetrazole-5-carboxylic acid ((1S,3R)-1-biphenyl-4-ylmethyl-4-methanesulfonylamino-3-methyl-4-oxo-butyl)-amide. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06 (d, J=7.1 Hz, 2 H), 1.66 (ddd, J=13.8, 10.9, 3.5 Hz, 1 H), 1.91 (ddd, J=13.7, 10.7, 3.4 Hz, 1 H), 2.54-2.63 (m, 1 H), 2.79-2.86 (m, 1 H), 2.86-2.93 (m, 1 H), 3.24 (s, 3 H), 4.15-4.28 (m, 1 H), 7.27 (d, J=8.3 Hz, 2 H), 7.30-7.36 (m, 1 H), 7.43 (t, J=7.6 Hz, 2 H), 7.55 (d, J=8.3 Hz, 2 H), 7.59-7.65 (m, 2 H), 9.19 (br. s., 1 H), 11.54 (br. s., 1 H).

Workup

  1. filtrationThe reaction is filtered off the catalyst
  2. concentrationis concentrated

Sources & evidence

ORD record
ord-b335b6666e7a4d8c816752c2c95717f8
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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