Borane → Methyl 3'-(2-(tert-butoxycarbonylamino)ethylamino)biphenyl-3-carboxylate

HRID 1069085Notes

Reaction equation

HRID 1069085 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)[CH:16]=[CH:17][CH:18]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)[CH:16]=[CH:17][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 54044428Methyl 3'-[(2-[[(tert-butoxy)carbonyl]amino]acetylamino)]-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 21191174Methyl 3'-(2-(tert-butoxycarbonylamino)ethylamino)biphenyl-3-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl 3′-[(2-[[(tert-butoxy)carbonyl]amino]acetylamino)]-[1,1′-biphenyl]-3-carboxylate (1.6 g) 0° C. was added a 1.0 M solution of borane in tetrahydrofuran (30 mL). The mixture was warmed to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous sodium bicarbonate and concentrated to leave a cloudy liquid that was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The separated organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel chromatography provided the title compound (740 mg). Electrospray MS (positive ion): M+Na 393.0

Workup

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. concentrationconcentrated
  3. customto leave a cloudy liquid that
  4. customwas partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-62cdd60502d8454b97074842ea184ee2
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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