Hydrochloric Acid → HCID 178480561, compound

HRID 1824342Notes

Reaction equation

HRID 1824342 reaction equation
C[O-].[Na+].C([S:7][C@@H:8]1[CH2:12][N:11]([CH3:13])[C@H:10]([C:14]([N:16]2[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:41])[CH2:23][NH:24][C:25]([NH:27][C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])=[NH:26])[CH2:17]2)=[O:15])[CH2:9]1)(=O)C.Cl>CO>[SH:7][C@@H:8]1[CH2:12][N:11]([CH3:13])[C@H:10]([C:14]([N:16]2[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:41])[CH2:23][NH:24][C:25]([NH:27][C:28]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=3)=[O:29])=[NH:26])[CH2:17]2)=[O:15])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 178477150HCID 178477150, compound

Product 1

HCID 178480561HCID 178480561, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 28% sodium methylate in methanol (0.5 ml) was added to a solution of (2S,4S)-4-acetylthio-1-methyl-2-[(3S)-3-[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]pyrrolidine (1.5 g) in methanol (30 ml) and stirred at room temperature for I hour. At the end of this time, to the resulting mixture was added 1N hydrochloric acid (2.73 ml) and concentrated in vacuo. The resulting residue was chromatographed on a reverse phase column (Cosmosil 75C18PREP (trade mark) manufactured by Nacalai tesque Inc.) using a mixture of acetonitrile and water as the eluant. The fractions containing the desired product were combined and concentrated in vacuo. The residue was powdered in a mixture of ethyl acetate and isopropyl ether. Powdery (2S,4S)-4-mercapto-1-methyl-2-[(3S)-3[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-yl-carbonyl]pyrrolidine (806 mg) was obtained by filtration.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was chromatographed on a reverse phase column (Cosmosil 75C18PREP (trade mark) manufactured by Nacalai tesque Inc.)
  3. additiona mixture of acetonitrile and water as the eluant
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated in vacuo
  6. additionThe residue was powdered in a mixture of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-ad69fb759735483386fd96c57e3a76e4
Source dataset
uspto-grants-2006_05
Patent number
US07041660B2

Reaction notes

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