HCID 178467360, compound → HCID 178467359, compound

HRID 1895512Notes

Reaction equation

HRID 1895512 reaction equation
[CH2:1]([O:3][C:4]1[N:5]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[NH:43][N:42]=[N:41][N:40]=3)=[CH:29][CH:28]=2)[C:6]2[C:12]([C:13]([NH:15][CH:16]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:17][S:18]C(=O)C)=[O:14])=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:2]>CO.[OH-].[Na+]>[SH:18][CH2:17][CH:16]([NH:15][C:13]([C:12]1[C:6]2[N:5]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]4[NH:43][N:42]=[N:41][N:40]=4)=[CH:29][CH:28]=3)[C:4]([O:3][CH2:1][CH3:2])=[N:8][C:7]=2[CH:9]=[CH:10][CH:11]=1)=[O:14])[CH2:22][CH:23]([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 178467360HCID 178467360, compound

Product 1

HCID 178467359HCID 178467359, compoundYield 1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Thioacetic acid S-[2-({2-ethoxy-3-[2′-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carbonyl}amino)-4-methylpentyl]ester (80 mg, 0.1 mmol) was dissolved in MeOH (5 mL) and 1M NaOH (5 mL). The mixture was stirred for 1 hour with nitrogen gas bubbling through the solution. The reaction was quenched with acetic acid (5 mL) and the mixture evaporated to dryness. The residue was purified using reverse phase preparative HPLC to afford the title compound (540 μg). ESMS [M+H]+ calcd for C30H33N7O2S, 555.3. found 556.4.

Workup

  1. custombubbling through the solution
  2. customThe reaction was quenched with acetic acid (5 mL)
  3. customthe mixture evaporated to dryness
  4. customThe residue was purified

Sources & evidence

ORD record
ord-bb834f7e15ce43bd8b71c27785234fc0
Source dataset
uspto-grants-2013_08
Patent number
US08513432B2

Reaction notes

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