Hydrochloric Acid → HCID 14124495, compound

HRID 1088261Notes

Reaction equation

HRID 1088261 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(=O)C)[CH2:14][C@H:13]2[CH2:21][C:22]([OH:24])=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC(OCC)=O.[CH3:33][NH2:34].Cl>O1CCCC1.C(OCC)(=O)C.C(O)C.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([SH:17])[CH2:14][C@H:13]2[CH2:21][C:22]([NH:34][CH3:33])=[O:24])=[O:11])=[CH:25][CH:26]=1)([O-:3])=[O:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 10928Ethyl chloroformateHCID 14830201(2R,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-carboxymethyl-4-acetylthiopyrrolidine

Product 1

HCID 14124495HCID 14124495, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2R,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-carboxymethyl-4-acetylthiopyrrolidine (153 mg) was dissolved in 2 ml of dry tetrahydrofuran, and 61 mg of triethylamine was added thereto. Ethyl chloroformate (65 mg) was added thereto at -10° to -15° C. under nitrogen stream, followed by stirring at the same temperature for 30 minutes. A 30% ethanol solution of methylamine (414 mg) was added thereto at -40° C., and stirring was continued at -20° to -30° C. for 1 hour. The reaction mixture was acidified with dilute hydrochloric acid, diluted with ethyl acetate, washed successively with water, a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel thin layer chromatography to obtain (2R,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methylaminocarbonylmethyl-4-mercaptopyrrolidine.

Workup

  1. customat -10° to -15° C.
  2. stirringat -40° C., and stirring
  3. waitwas continued at -20° to -30° C. for 1 hour
  4. washwashed successively with water
  5. dry with materiala saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-b0e8c76c641f416ebf7aab8289fd6064
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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