Sodium Bicarbonate → HCID 20786541, compound

HRID 2182853Notes

Reaction equation

HRID 2182853 reaction equation
[N+](C1C=C(S(CC[O:15][C:16](=[O:63])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:62])[CH2:24][O:25][C:26]2[CH:31]=[C:30]([CH3:32])[C:29]([S:33]([N:36]3[C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=4[N:38]=[C:37]3[S:45]([CH2:47][C:48]3[C:53]([CH3:54])=[C:52]([O:55][CH2:56][C:57]([F:60])([F:59])[F:58])[CH:51]=[CH:50][N:49]=3)=[O:46])(=[O:35])=[O:34])=[C:28]([CH3:61])[CH:27]=2)(=O)=O)C=CC=1)([O-])=O.C([O-])(O)=O.[Na+:68]>C1COCC1.O>[Na+:68].[CH3:32][C:30]1[CH:31]=[C:26]([CH:27]=[C:28]([CH3:61])[C:29]=1[S:33]([N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[S:45]([CH2:47][C:48]1[C:53]([CH3:54])=[C:52]([O:55][CH2:56][C:57]([F:58])([F:59])[F:60])[CH:51]=[CH:50][N:49]=1)=[O:46])(=[O:35])=[O:34])[O:25][CH2:24][C:23]([NH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]([O-:63])=[O:15])=[O:62]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20786374HCID 20786374, compound2×

Product 1

HCID 20786541HCID 20786541, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 6-[2-(3,5-dimethyl-4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)-pyridin-2-ylmethanesulfinyl]-benzimdazole-1-sulfonyl}phenoxy)acetylamino]hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 18, 420 mg, 0.45 mmol) and of NaHCO3 (42 mg, 0.49 mmol) in THF-H2O (6 mL-3 mL) was heated to 70° C. for 1 h. Then volatile materials were removed, the residual gummy oil was dissolved in CH2Cl2 and the mixture was filtered to remove un-dissolved solid. The filtrate was concentrated to dryness and the residual semi-solid was treated with diethyl ether to precipitate a solid which was briefly treated with CH3CN. The solid was collected from CH3CN suspension by filtration to give Compound 6 (170 mg 50%) as a white solid.

Workup

  1. customThen volatile materials were removed
  2. dissolutionthe residual gummy oil was dissolved in CH2Cl2
  3. filtrationthe mixture was filtered
  4. customto remove
  5. dissolutionun-dissolved solid
  6. concentrationThe filtrate was concentrated to dryness
  7. additionthe residual semi-solid was treated with diethyl ether
  8. customto precipitate a solid which
  9. additionwas briefly treated with CH3CN
  10. filtrationThe solid was collected from CH3CN suspension by filtration

Sources & evidence

ORD record
ord-97dea8eb38344bb0adebae8d7afd78b4
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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