Water → HCID 5282536, compound

HRID 1611010Notes

Reaction equation

HRID 1611010 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[S:5][C:6]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].O.C(=O)(O)[O-].[Na+]>CC(C)C(O)=O>[CH3:4][CH:8]([CH3:9])[CH2:7][NH:3][C:4]1[S:5][C:6]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 5282535HCID 5282535, compound

Product 1

HCID 5282536HCID 5282536, compoundYield 191%

Reagents, catalysts & solvents 1

HCID 6590Isobutyric AcidSolvent

Procedure

Sodium borohydride (1.3 g) was added in 10 portions over 5 hours to a stirred solution of ethyl 2-amino-5-(1-naphthalenylmethyl)-3-thiophenecarboxylate (5.50 g) in 2-methylpropanoic acid (40 ml) at 0° C. The mixture was stirred at room temperature for 16 hours then further sodium borohydride (1.8 g) was added in 10 portions over 8 hours and stirring continued for a further 16 hours. The solution was poured into water (1000 ml), neutralized with sodium bicarbonate and extracted with ethyl acetate (2×500 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ether:hexane (1:3) to give the subtitle compound (6.20 g):

Workup

  1. stirringstirring
  2. waitcontinued for a further 16 hours
  3. extractionextracted with ethyl acetate (2×500 ml)
  4. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography over silica
  8. washeluting with ether:hexane (1:3)

Sources & evidence

ORD record
ord-75f5275d44804333bba955a63e2ce042
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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