Hydrochloric Acid → HCID 16747646, compound

HRID 1515358Notes

Reaction equation

HRID 1515358 reaction equation
[CH3:1][C:2](=[CH2:37])[C:3]#[C:4][C@@H:5]([N:16]1[CH2:21][CH2:20][C@@H:19]([CH2:22][C:23]([O:25]C)=[O:24])[CH2:18][C@H:17]1[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)[C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1.[Li+].[OH-].Cl>C1COCC1.O>[CH3:37][C:2](=[CH2:1])[C:3]#[C:4][C@@H:5]([N:16]1[CH2:21][CH2:20][C@@H:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][C@H:17]1[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][CH:28]=1)[C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:13])[F:14])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57878526HCID 57878526, compound

Product 1

HCID 16747646HCID 16747646, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester from Step 2 (0.146 g, 0.28 mmol) and LiOH (0.133 g, 5.6 mmol) in THF (3 ml) and water (3 ml) was stirred at rt for 16 hrs. The reaction mixture was acidified to pH6 with 2N HCl and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (silica, 1-2% MeOH/DCM) to give the acid (0.101 g, 71%). 1H NMR (360 MHz, CD3OD): δ 1.26-1.38 (1H, m), 1.51 (1H, q, J 12.1), 1.77 (1H, m), 1.90-1.98 (2H, m), 2.03 (3H, s), 2.24 (2H, d, J 6.9), 2.43-2.57 (2H, m), 3.74 (1H, dd, J 2.6, 11.4), 4.70 (1H, s), 5.39 (1H, m), 5.46 (1H, s), 7.70-7.72 (4H, m), 7.80 (1H, d, J 8.2), 8.17 (1H, d, J 8.1), 8.82 (1H, s).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (silica, 1-2% MeOH/DCM)

Sources & evidence

ORD record
ord-774d093ddf8a4236a7fff753426689d4
Source dataset
uspto-grants-2012_07
Patent number
US08222418B2

Reaction notes

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