Sulfuric Acid → HCID 178418982, compound

HRID 1797455Notes

Reaction equation

HRID 1797455 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:33])[CH2:15][NH:16][C:17]([NH:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[O:21])=[NH:18])[CH2:9]1)=O)(C)(C)C.[S:34](=[O:38])(=[O:37])([OH:36])[OH:35].C(OC(C)C)(C)C>CO>[S:34]([O:36][S:34]([OH:37])(=[O:36])=[O:35])([OH:35])(=[O:38])=[O:37].[N+:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:22][C:20]([NH:19][C:17](=[NH:18])[NH:16][CH2:15][C:14]([NH:13][C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[O:33])=[O:21])=[CH:25][CH:26]=1)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7914Diisopropyl EtherHCID 178418987HCID 178418987, compound

Product 1

HCID 178418982HCID 178418982, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
42.5 °C

Procedure

(S)-1-(t-butyloxycarbonyl)-3-[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidine ½ sulfate (350 g, purity 86%) was added to a solution of concentrated sulfuric acid (234 g) and methanol (2.45 L) and the mixture was stirred at from 40 to 45° C. for 2.5 hours. The reaction mixture was cooled to from 20 to 30° C., and then was stirred at the same temperature for 0.5 hours. Diisopropyl ether (3.5 L) was added to the mixture, which was stirred at the same temperature for 1 hour. The crystals which precipitated were collected by filtration to give the title compound (328 g, purity 95.8%, yield 95.4%)

Workup

  1. temperatureThe reaction mixture was cooled to from 20 to 30° C.
  2. stirringwas stirred at the same temperature for 0.5 hours
  3. stirringwas stirred at the same temperature for 1 hour
  4. customThe crystals which precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e6ab71e892eb4913bb1dfc2c423c3190
Source dataset
uspto-grants-2006_04
Patent number
US07034150B2

Reaction notes

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