Hydrochloric Acid → HCID 67253415, compound

HRID 1711665Notes

Reaction equation

HRID 1711665 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12]CC)=[O:11])[N:7]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH2:21][N:20]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:19][CH2:18]3)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O.Cl>C1COCC1.CCO.O>[CH2:28]([O:27][C:25]([N:20]1[CH2:19][CH2:18][C:17]2[C:22](=[CH:23][CH:24]=[C:15]([N:7]3[C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6]3)[CH:16]=2)[CH2:21]1)=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67253043Phenylmethyl 6-[3-(1,1-dimethylethyl)-5-(ethoxycarbonyl)-1H-pyrazol-1-yl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 67253415HCID 67253415, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirring solution of benzyl 6-(3-t-butyl-5-(ethoxycarbonyl)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.160 g, 0.347 mmol) in 1:1:1 THF/EtOH/H2O (3 ml) at 22° C. was added LiOH.H2O (0.0727 g, 1.73 mmol). After 3 h, the completed reaction was acidified (pH 2-3) with 1M HCl and extracted with EtOAc (3×). The combined organic phases were washed with brine (2×), dried (MgSO4), filtered and evaporated to afford 1-(2-(benzyloxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylic acid (0.16 g, 106% yield) as an oil which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.41-7.31 (m, 5H), 7.328-7.20 (m, 3H), 6.91 (s, 1H), 5.15 (s, 2H), 4.65 (brm, 2H), 3.66 (brs, 2H), 2.86 (t, 2H, J=6.0 Hz), 1.29 (s, 9H); MS (ESI) m/z: 434.2 (M+H+).

Workup

  1. customthe completed reaction
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic phases were washed with brine (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ede2d0a47abf45b485e9871bf6b50c5f
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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