Citric Acid → HCID 67049798, compound

HRID 217632Notes

Reaction equation

HRID 217632 reaction equation
[BH4-].[Li+].[C:3]([O:7][C:8]([NH:10][C:11]1[C:12]([NH:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25](OC)=[O:26])=[CH:21][N:20]=2)=[O:18])=[CH:13][S:14][CH:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[C:3]([O:7][C:8]([NH:10][C:11]1[C:12]([NH:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][N:20]=2)=[O:18])=[CH:13][S:14][CH:15]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 312751,4-DioxaneHCID 4148881Lithium borohydride2×HCID 67050039N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methoxycarbonylpyridine-2-carboxylic acid amide

Product 1

HCID 67049798HCID 67049798, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, lithium tetrahydroborate (1.5 g, 70 mmol) was added to a mixed solution of N-(4-t-butoxycarbonylaminothiophen-3-yl)-5-methoxycarbonylpyridine-2-carboxylic acid amide (Reference Compound No. 2-1, 24 g, 64 mmol) in THF (1.3 L)-1,4-dioxane (1.3 L), and then the reaction mixture was stirred at same temperature overnight. Lithium tetrahydroborate (0.30 g, 14 mmol) was added thereto and the mixture was stirred at room temperature for 2 hours. Under ice cooling, water (0.40 L) and 10% aqueous citric acid solution (25 mL) were added thereto. The precipitates were filtered off and the filtrate was evaporated under reduced pressure. Water (0.30 L) was added thereto and the precipitates were filtered and dried under reduced pressure to give 21 g of the title reference compound as a pale yellow solid. (Yield 95%)

Workup

  1. filtrationThe precipitates were filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. additionWater (0.30 L) was added
  4. filtrationthe precipitates were filtered
  5. customdried under reduced pressure
  6. customto give 21 g of the title reference compound as a pale yellow solid

Sources & evidence

ORD record
ord-c78e45c4a1954f66bc55c6260c9fec27
Source dataset
uspto-grants-2012_06
Patent number
US08198271B2

Reaction notes

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