Sodium Bicarbonate → HCID 54060004, compound

HRID 1489843Notes

Reaction equation

HRID 1489843 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10](=[O:28])[C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16](=[O:27])[CH2:17][NH:18][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)(O)[O-].[Na+].[Cl:36][CH2:37]S(OCl)(=O)=O>C(Cl)Cl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:28])[C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16](=[O:27])[CH2:17][NH:18][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:37][Cl:36])=[O:24])=[CH:29][CH:30]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 69835878HCID 69835878, compoundHCID 131719457HCID 131719457, compound

Product 1

HCID 54060004HCID 54060004, compoundYield 87.1%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.09 g of Compound (23) obtained in the step (b) in 70 ml of methylene chloride were added 1.85 g of sodium bicarbonate in 70 ml of water, 249 mg of tetrabutylammonium hydrogen sulfate and 1.57 g of ClCH2SO3Cl, and the reaction mixture was stirred for 140 minutes at room temperature. After reaction, the organic layer was separated and washed with 4% sodium bicarbonate aqueous solution and saline, and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 3.00 g of [N-(4-chloromethyloxycarbonylbutanoyl)glycyl]-L-proline p-nitrobenzyl ester as pale yellowish oil. Then, a mixture solution of 2.86 g of the compound obtained above and 1.83 g of sodium iodide in 20 ml of acetonitrile was refluxed for 2 hours. After reaction, the solvent was removed and the resulting residue was dissolved in 70 ml of ethyl acetate. The organic layer was washed with 0.1 N sodium thiosulfate aqueous solution and saline, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (methylene chloride-acetone) to give 2.35 g of [N-(4-iodomethyloxycarbonylbutanoyl)glycyl]-L-proline P-nitrobenzyl ester [Compound (24)] as yellowish oil.

Workup

  1. customAfter reaction
  2. customthe organic layer was separated
  3. washwashed with 4% sodium bicarbonate aqueous solution and saline
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ac456ae7cd41414897036fb1368f99f6
Source dataset
uspto-grants-1997_10
Patent number
US05679790

Reaction notes

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