Hydrochloric Acid → HCID 86588729, compound

HRID 1072118Notes

Reaction equation

HRID 1072118 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1.N1C=CC=CC=1.[Li+].[BH4-].Cl>C1COCC1>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH:16]=3)=[CH:13][CH:14]=2)[S:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 4148881Lithium borohydrideHCID 86588730HCID 86588730, compound

Product 1

HCID 86588729HCID 86588729, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.69 g (0.009 mol) of tert-butyl [4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-yl]methylcarbamate, 6 ml of THF and 7.3 ml of pyridine are introduced, in order, into a 50 ml three-necked round-bottomed flask. The mixture is placed under nitrogen and 10 ml of a freshly prepared 2 M LiBH4 solution (0.02 mol) in THF are added dropwise. After stirring for 30 minutes at room temperature, the mixture is heated under reflux for 16 hours. The reaction medium is poured over 32 ml of a 1 N HCl solution and the THF is evaporated under vacuum. The precipitate obtained is filtered. After drying, the crude product (2.75 g) is chromatographed on 95 g of silica gel, eluting with a heptane/ethyl acetate=3/7 mixture. 2.45 g (66%) of tert-butyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]methylcarbamate are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. customthe THF is evaporated under vacuum
  4. customThe precipitate obtained
  5. filtrationis filtered
  6. customAfter drying
  7. customthe crude product (2.75 g) is chromatographed on 95 g of silica gel
  8. washeluting with a heptane/ethyl acetate=3/7 mixture

Sources & evidence

ORD record
ord-45bcb42d1ef4471eaa85342872d29509
Source dataset
uspto-grants-2005_06
Patent number
US06908939B2

Reaction notes

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