Sodium Carbonate → HCID 58042873, compound

HRID 564060Notes

Reaction equation

HRID 564060 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[S:21][C:20]([C:22](O)=[O:23])=[CH:19][CH:18]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.[K].S([O-])(O)(=O)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[S:21][C:20]([CH2:22][OH:23])=[CH:19][CH:18]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 67007765HCID 67007765, compound

Product 1

HCID 58042873HCID 58042873, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 86623685HCID 86623685, compoundSolvent

Conditions

Temperature
50 °C

Procedure

To 530 mg (1.49 mmol) 5-[2-(4-benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-thiophene-2-carboxylic acid (preparation 11c) in 15 mL THF is added at RT 266 mg (1.64 mmol) CDI. The reaction mixture is stirred 30 min at 50° C. and is then poured into a solution of 169 mg (4.47 mmol) sodium borohydride in 40 mL water. The mixture is stirred 1 h at RT, diluted with saturated aqueous potassium-hydrogen-sulfate-solution and stirred for another 20 min. The mixture is neutralized with saturated aqueous Na2CO3-solution. The aqueous phase is extracted three times with EtOAc/MeOH. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated to afford the product.

Workup

  1. stirringThe mixture is stirred 1 h at RT
  2. stirringstirred for another 20 min
  3. extractionThe aqueous phase is extracted three times with EtOAc/MeOH
  4. dry with materialThe combined organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customto afford the product

Sources & evidence

ORD record
ord-afb567c2ec41402a9271b4076c71a2c4
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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