Diethyl Ether → HCID 131720086, compound

HRID 264005Notes

Reaction equation

HRID 264005 reaction equation
CC(OC([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])=O)(C)C.[CH2:19]([O:26][C:27](=[O:33])[C@@H:28]1[CH2:32][CH2:31][CH2:30][NH:29]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.O1CCOCC1.C(Cl)(Cl)[Cl:42].C(OCC)C>O1CCOCC1.CO>[CH3:15][S:12]([CH2:11][CH2:10][C@H:9]([NH2:8])[C:16]([OH:18])=[O:17])(=[O:13])=[O:14].[ClH:42].[CH2:19]([O:26][C:27](=[O:33])[C@@H:28]1[CH2:32][CH2:31][CH2:30][NH:29]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 204431481,4-Dioxane hydrochlorideHCID 131720087HCID 131720087, compound

Product 1

HCID 131720086HCID 131720086, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-Boc-L-methionine sulfone-L-proline-O-benzyl ester (23.5 g, 50 mmole) in dry dioxane (300 mL) was added 100 mL of a 4M HCl/dioxane solution. The mixture was then stirred at room temperature for 1 hour until the starting material disappeared as shown by thin layer chromatography analysis (silica, 10% chloroform in methanol). Diethyl ether was added to the mixture to precipitate the title compound as a white hydrochloride salt. The mixture was filtered on a Buchner funnel and the solid was then dried under high vacuum to give 20.16 g (100%) of the title compound as a white solid.

Workup

  1. customto precipitate the title compound as a white hydrochloride salt
  2. filtrationThe mixture was filtered on a Buchner funnel
  3. customthe solid was then dried under high vacuum

Sources & evidence

ORD record
ord-67defb344ab74c369d089cf0a7140b03
Source dataset
uspto-grants-1997_07
Patent number
US05646165

Reaction notes

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