Hydrochloric Acid → HCID 131733876, compound

HRID 708902Notes

Reaction equation

HRID 708902 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:37])[CH2:9][O:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([F:36])[C:17]([O:30][CH2:31][CH2:32][CH2:33][O:34][CH3:35])=[C:18]([CH:29]=2)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22]C(C)(C)C)=[O:12])=[C:4]([CH3:38])[CH:3]=1.Cl.C(N(CC)C(C)C)(C)C.[CH2:49](OC(ON1C(=O)CCC1=O)=O)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:37])[CH2:9][O:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([F:36])[C:17]([O:30][CH2:31][CH2:32][CH2:33][O:34][CH3:35])=[C:18]([CH:29]=2)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:12])=[C:4]([CH3:38])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 118101230HCID 118101230, compound

Product 1

HCID 131733876HCID 131733876, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 28B (450 mg, 0.753 mmol) in EtOAc (6 mL), was added HCl (4N, 6 mL). The mixture was stirred rt for 2 h, and concentrated. The residue was dissolved in DMF (10 ml), N,N-diisopropylethylamine (0.525 ml, 3.01 mmol) was added, followed by N-(benzyloxycarbonyloxy) succinimide (206 mg, 0.828 mmol). The mixture was stirred rt for 1 h, quenched with water, extracted with EtOAc (3×30 ml). The organic layer was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0-60% EtOAc in hexanes) to give 28C (376 mg, 0.595 mmol, 79% yield). MS (ESI) m/z: 631.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DMF (10 ml)
  3. stirringThe mixture was stirred rt for 1 h
  4. customquenched with water
  5. extractionextracted with EtOAc (3×30 ml)
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ec41e9678f954c5d8874187591012d5f
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

Loading…