HCID 86600020, compound → HCID 44474956, compound

HRID 1814249Notes

Reaction equation

HRID 1814249 reaction equation
[NH2:1][C:2](=O)[C@H:3]([NH:5][C:6](=[O:22])[O:7][CH2:8][CH:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:4]>C1COCC1>[NH2:1][CH2:2][C@H:3]([NH:5][C:6](=[O:22])[O:7][CH2:8][CH:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:16]2[C:21]1=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:4]

Participants

3

Reactant 1

HCID 86600020HCID 86600020, compound

Product 1

HCID 44474956HCID 44474956, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from example 9, step (a) (6.9 g) in THF (100 ml) was added borane-methylsulfide complex (4.4 ml) and the mixture heated under reflux for 2 hours. The mixture was carefully quenched by the addition of methanol (100 ml), evaporated to dryness and the residue taken up into methanol (100 ml) and acidified to pH 1-2 with concentrated hydrochloric acid. Heated under reflux for 30 mins then evaporated to dryness. The residue was triturated with ether to give a solid, which was collected by filtration, dissolved in water and the free base precipitated by the addition of aqueous sodium bicarbonate solution to give the subtitle compound (3.1 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. customThe mixture was carefully quenched by the addition of methanol (100 ml)
  4. customevaporated to dryness
  5. temperatureHeated
  6. temperatureunder reflux for 30 mins
  7. customthen evaporated to dryness
  8. customThe residue was triturated with ether
  9. customto give a solid, which
  10. filtrationwas collected by filtration
  11. dissolutiondissolved in water
  12. customthe free base precipitated by the addition of aqueous sodium bicarbonate solution

Sources & evidence

ORD record
ord-80af4b3925274bfabf90781ce2ff3a66
Source dataset
uspto-grants-2005_04
Patent number
US06875868B2

Reaction notes

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