Tetrahydrofuran → HCID 13096831, compound

HRID 1164547Notes

Reaction equation

HRID 1164547 reaction equation
Cl.[CH3:2][N:3]1[C:7]([S:8][CH2:9][CH:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:21])=[C:17]([OH:20])[CH:18]=3)[CH2:13][CH2:12][NH:11]2)=[N:6][N:5]=[N:4]1.C(=O)(O)[O-].[Na+].O1CCCC1.Cl[C:33]([O:35][CH2:36][C:37]([Cl:40])([Cl:39])[Cl:38])=[O:34]>O>[CH3:2][N:3]1[C:7]([S:8][CH2:9][CH:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:21])=[C:17]([OH:20])[CH:18]=3)[CH2:13][CH2:12][N:11]2[C:33]([O:35][CH2:36][C:37]([Cl:40])([Cl:39])[Cl:38])=[O:34])=[N:6][N:5]=[N:4]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium Bicarbonate2×HCID 12773873HCID 12773873, compound

Product 1

HCID 13096831HCID 13096831, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 1-(1-methyl-1H-tetrazol-5-yl)thiomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (50 g) in water (300 ml) was dissolved at 61° to 65° C. To the solution was added sodium bicarbonate (13.3 g) over 15 minutes at the same temperature. Tetrahydrofuran (250 ml) was added to the suspension at 50° C. The suspension was cooled and weakly alkalified by adding sodium bicarbonate (30 g) at 0° to 3° C. To the mixture was added 2,2,2-trichloroethyl chloroformate (40.2 g) over 30 minutes below 3° C. The resulting mixture was stirred for 30 minutes at 0° C. Water (300 ml) was added to the reaction mixture and the mixture was twice extracted with ethyl acetate (900 ml and 600 ml). The extract was washed with a sodium chloride aqueous solution (300 ml) and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized with ether to give 1-(1-methyl-1H-tetrazol-5-yl)thiomethyl-2-(2,2,2-trichloroethoxycarbonyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (40.4 g), mp 201° to 207° C.

Workup

  1. dissolutionwas dissolved at 61° to 65° C
  2. temperatureThe suspension was cooled
  3. extractionthe mixture was twice extracted with ethyl acetate (900 ml and 600 ml)
  4. washThe extract was washed with a sodium chloride aqueous solution (300 ml)
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was crystallized with ether

Sources & evidence

ORD record
ord-928a86d4446246e7acb2fb446eb3c4bf
Source dataset
uspto-grants-1983_01
Patent number
US04370332

Reaction notes

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