Dichloromethane → HCID 18645972, compound

HRID 1086476Notes

Reaction equation

HRID 1086476 reaction equation
[CH3:1][C@H:2]([NH:15][CH2:16][C@@H:17]([C:19]1[CH:20]=[CH:21][C:22]2[N:23](N=N[N:27]=2)[CH:24]=1)[OH:18])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][CH:5]=1.O.O.[Cl:30][Sn]Cl.C(Cl)[Cl:34].[OH-].[Na+]>CO.Cl.CCOCC>[ClH:30].[ClH:34].[NH2:27][C:22]1[N:23]=[CH:24][C:19]([C@H:17]([CH2:16][NH:15][C@@H:2]([CH3:1])[CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=3)[NH:6][CH:5]=2)[OH:18])=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 15137737HCID 15137737, compound

Product 1

HCID 18645972HCID 18645972, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of this tetrazole (391 mg) in 10 ml of methanol, 0.1 ml of concentrated HCl and 473 mg of SnCl2.2H2O were added. The reaction mixture was heated at reflux under nitrogen for 16 hours and then poured into a solution of CH2Cl2 (45 ml) and 1N NaOH solution (64 ml). The mixture was stirred for 20 minutes and the layers then separated. The aqueous phase was further extracted with CH2Cl2. The combined organic extracts were backed washed with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. The solution was concentrated and the crude residue (309 mg) was purified by preparative TLC on silica gel (90:10:1 CH2Cl2 :MeOH:NH4OH) to afford pure product which was converted to its hydrochloride salt with ethanolic HCl. The salt was isolated by dilution with ether and filtration, 240 mg; mp 264° C.; [α]D 25°=-8.45 (c= 1.0, MeOH); Analysis: Calculated for C19H24N4O2.2HCl: C, 55.21; H, 6.34; N, 13.56. Found: C, 54.82; H, 6.60; N, 13.08.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 16 hours
  3. customthe layers then separated
  4. extractionThe aqueous phase was further extracted with CH2Cl2
  5. washThe combined organic extracts were backed washed with saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated
  8. customthe crude residue (309 mg) was purified by preparative TLC on silica gel (90:10:1 CH2Cl2 :MeOH:NH4OH)
  9. customto afford pure product which

Sources & evidence

ORD record
ord-d05080c4465644c080a6ace4183dabdf
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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