Methanol → HCID 66719276, compound

HRID 430640Notes

Reaction equation

HRID 430640 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][C@@H:11]([C:16]([OH:18])=[O:17])[NH:12][CH2:13]2)=[CH:8][CH:7]=1.[CH3:19]O>>[ClH:3].[OH:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][C@@H:11]([C:16]([O:18][CH3:19])=[O:17])[NH:12][CH2:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2733173L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 66719276HCID 66719276, compoundYield 89%

Conditions

Temperature
25 °C

Procedure

Thionyl chloride (1.629, 13.6 mmol) was added dropwise to a solution of (3S)-7-hydroxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (0.75 g, 3.9 mmol) in methanol (30 mL) at about 0° C. under N2. The solution was warmed to about 25° C. and stirred for about 6 h, then was concentrated. The residue was washed with ether, followed by 1:1 ether pentane and dried under vacuum to yield 0.85 g of product as a white solid (89% yield). 1H NMR (d6DMSO) δ 3.09 (m, 2H); 3.78 (s, 3H); 4.23 (apparent s, 2H); 4.51 (m, 1H); 6.61 (s, 1H); 6.72 (d, J=3 Hz, 1H); 7.04 (d, J=3 Hz, 1H).

Workup

  1. concentrationwas concentrated
  2. washThe residue was washed with ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-20ddd3d9707b494e9d61dcb1da86b439
Source dataset
uspto-grants-2001_11
Patent number
US06323215B1

Reaction notes

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