Sodium Bicarbonate → HCID 21248818, compound

HRID 1194928Notes

Reaction equation

HRID 1194928 reaction equation
[Cl:1][CH2:2][O:3]S(Cl)(=O)=O.[N+:8]([C:11]1[CH:34]=[CH:33][C:14]([CH2:15][O:16][C:17]([NH:19][CH2:20][C:21]([NH:23][C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)=[O:22])=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9].C(=O)(O)[O-].[Na+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[Cl:1][CH2:2][O:3][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([NH:23][C:21](=[O:22])[CH2:20][NH:19][C:17]([O:16][CH2:15][C:14]2[CH:33]=[CH:34][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=2)=[O:18])=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfateHCID 212489994-[N-(4-Nitrobenzyloxycarbonyl)glycylamino]-benzoic acid

Product 1

HCID 21248818HCID 21248818, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

A solution of chloromethylchlorosulphate (2.21 g) in dichloromethane (5 ml) was added dropwise to a stirred mixture of 4-[N-(4-nitrobenzyloxycarbonyl)glycylamino]-benzoic acid (4.00 g), sodium bicarbonate (3.00 g) and tetrabutylammonium hydrogen sulphate (0.493 g) in dichloromethane-water (1:1, 50 ml). The mixture was stirred at room temperature for 3 h. The organic phase was separated and the aqueous phase washed with dichloromethane (50 ml). The combined organic extracts were dried (MgSO4), concentrated to low volume and applied to a column of Kieselgel 60. Elution with 50% ethyl acetate/hexane afforded the title compound as a white solid (46%); m.p. 163°-5° (ethyl acetate), (Found: C, 51.49; H, 3.79; N, 9.76. C18H16N3O7Cl requires C, 51.26; H, 3.82; N, 9.96%); νmax (Nujol) 3400, 3300, 1740, 1685, and 1610 cm-1 ; δH (CDCl3 /D6 -DMSO) 3.95 (2H, d, J 6.0 Hz), 5.25 (2H, s), 5.97 (2H, s), and 7.35-8.20 (10H, m).

Workup

  1. customThe organic phase was separated
  2. washthe aqueous phase washed with dichloromethane (50 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated to low volume
  5. washElution with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-416471973b87464a89c42d243f4e4cd6
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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