Hydrochloric Acid → HCID 67340021, compound

HRID 1045109Notes

Reaction equation

HRID 1045109 reaction equation
[H-].[Na+].C[O:4][C:5](=[O:8])[CH2:6][OH:7].[C:9]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:14]=[CH:13][C:12]([C:15]2[CH:35]=[CH:34][C:18]3[N:19]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20](S(C)(=O)=O)=[N:21][C:17]=3[CH:16]=2)=[CH:11][CH:10]=1.Cl>C1COCC1.O.C(#N)C.O>[C:9]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:14]=[CH:13][C:12]([C:15]2[CH:35]=[CH:34][C:18]3[N:19]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20]([O:7][CH2:6][C:5]([OH:4])=[O:8])=[N:21][C:17]=3[CH:16]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 67338572HCID 67338572, compound2×

Product 1

HCID 67340021HCID 67340021, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A 20 mL scintillation vial equipped with a septum cap and a magnetic stirring bar was charged under N2 with NaH (6.0 mg, 60% suspension in mineral oil, 0.15 mmol). A solution of hydroxyacetic acid methyl ester (18.0 mg, 0.200 mmol) in THF (2.0 mL) was added dropwise to the vial and the resulting mixture was stirred at rt for 10 min. Then, a solution of 5-biphenyl-4-yl-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (compound 46-1, 51.3 mg, 0.100 mmol) in THF (1 mL) was added. The resulting mixture was stirred at rt for 10 mM, then diluted by dropwise addition of 1:1 ACN/water (2 mL) and left to stir at rt for 30 min. The reaction mixture was then diluted with water (5 mL), acidified with 5% aqueous HCl and extracted with EtOAc (three times, 3 mL). The organic layers were combined and washed with 5% aqueous HCl and water, and evaporated to dryness in vacuo to give the title compound as pale yellow solid. LR-MS (API-ES): mixture of two N-SEM isomers, calculated for C27H29ClN2O4Si 508.2, observed m/e 509.0 [(M+H)+, 100%], 465 (Rt 3.74 min). The compound was used in the next step without further purification.

Workup

  1. customA 20 mL scintillation vial equipped with a septum
  2. customcap
  3. stirringThe resulting mixture was stirred at rt for 10 mM
  4. waitleft
  5. stirringto stir at rt for 30 min
  6. extractionextracted with EtOAc (three times, 3 mL)
  7. washwashed with 5% aqueous HCl and water
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-22f7c3b58d134862bc146fbd112a2e03
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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