Sodium Bicarbonate → 6-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetylamino]hexanoic Acid

HRID 2182857Notes

Reaction equation

HRID 2182857 reaction equation
[N+](C1C=C(S(CC[O:15][C:16](=[O:61])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:60])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([N:35]3[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=4[N:37]=[C:36]3[S:44]([CH2:46][C:47]3[C:52]([CH3:53])=[C:51]([O:54][CH2:55][C:56]([F:59])([F:58])[F:57])[CH:50]=[CH:49][N:48]=3)=[O:45])(=[O:34])=[O:33])=[CH:28][CH:27]=2)(=O)=O)C=CC=1)([O-])=O.C([O-])(O)=O.[Na+]>CC#N.O.CC(O)C>[CH3:53][C:52]1[C:47]([CH2:46][S:44]([C:36]2[N:35]([S:32]([C:29]3[CH:28]=[CH:27][C:26]([O:25][CH2:24][C:23]([NH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]([OH:61])=[O:15])=[O:60])=[CH:31][CH:30]=3)(=[O:34])=[O:33])[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[N:37]=2)=[O:45])=[N:48][CH:49]=[CH:50][C:51]=1[O:54][CH2:55][C:56]([F:58])([F:57])[F:59]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 207863756-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester2×

Product 1

HCID 224793036-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetylamino]hexanoic AcidYield 43.1%

Reagents, catalysts & solvents 1

HCID 22159075CH3CN-H2O iPrOHSolvent

Procedure

A solution of 6-[2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 20, 450 mg, 0.50 mmol) and of NaHCO3 (50 mg, 0.60 mmol, 1.2 eq) in CH3CN-H2O-iPrOH (2 mL:1 mL:1 mL) was heated to 70° C. for 1.5 h. Thereafter volatile materials were removed by evaporation, the residual gummy oil was dissolved in CH2Cl2, and the mixture was filtered to remove undissolved solid. The filtrate was dried and concentrated under reduced pressure. The residual oil was purified by silica gel column to yield 150 mg of Compound 7 as a light brown foam.

Workup

  1. customThereafter volatile materials were removed by evaporation
  2. dissolutionthe residual gummy oil was dissolved in CH2Cl2
  3. filtrationthe mixture was filtered
  4. customto remove undissolved solid
  5. customThe filtrate was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residual oil was purified by silica gel column

Sources & evidence

ORD record
ord-631870ad0585409d8c3f4e6ea9f94fdd
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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