HCID 10044381, compound → HCID 70025041, compound

HRID 478951Notes

Reaction equation

HRID 478951 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH3:16])[CH2:10][N:9](C(OC(C)(C)C)=O)[C@H:8]([C:24]([OH:26])=[O:25])[CH2:7]2)[CH3:2].Cl.CC(O)C>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH3:16])[CH2:10][NH:9][C@H:8]([C:24]([OH:26])=[O:25])[CH2:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 10044381HCID 10044381, compoundHCID 21912024Isopropanol hydrochloride

Product 1

HCID 70025041HCID 70025041, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-1,2,3,4-tetrahydro-6,7-diethoxy-2-(tert-butyloxycarbonyl)-3-isoquinolinecarboxylic acid (example 4) (18.3 g, 0.05 mol), 20% HCl/IPA solution (18.3 g, 0.1 mol) in ethyl acetate (100 mL) was stirred at 40° C. for 3 hrs. The resulting suspension was cooled to room temperature, filtered, and rinsed with ethyl acetate (2×30 mL). The solids were dried under vacuum to give 12.1 g of (S)-1,2,3,4-tetrahydro-6,7-diethoxy-3-isoquinolinecarboxylic acid. Yield 81%. 1H NMR (DMSO-d6) δ: 1.32 (t, J=6.9 Hz, 6H, CH2CH3), 3.03 (dd, J=16.7, 10.9 Hz, 1H, CHHCHCOOH), 3.21 (dd, J=16.7, 4.9 Hz, 1H, CHHCHCOOH), 3.9-4.06 (m, 2H, CH2CH3), 4.2 (br s, 2H, CH2N), 4.33 (dd, J=10.9, 4.9 Hz, 1H, CHCOOH), 6.84, 6.85 (s, 2H, PhH), 9.96 (br s, 2H, NHHCl).

Workup

  1. filtrationfiltered
  2. washrinsed with ethyl acetate (2×30 mL)
  3. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-55d4933910dc4d2795d8583967a9bd37
Source dataset
uspto-grants-2003_11
Patent number
US06642384B1

Reaction notes

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