Hydrochloric Acid → methyl 2-(R)-[(piperazine-1-sulfonyl)amino]propionate

HRID 843027Notes

Reaction equation

HRID 843027 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][N:12]([S:15]([NH:18][C@H:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])(=[O:17])=[O:16])[CH2:11][CH2:10]1)=O)(C)(C)C.COC(=O)[C@@H](C(C)C)N.COC(=O)[C@@H](C)N>O1CCOCC1.C(Cl)Cl>[N:12]1([S:15]([NH:18][C@H:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])(=[O:17])=[O:16])[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 89020methyl D-alaninateHCID 2305648(R)-methyl 2-amino-3-methylbutanoateHCID 18727245methyl 2-(R)-[(4-tert-butoxycarbonylpiperazine-1-sulfonyl)amino]propionate

Product 1

HCID 18727249methyl 2-(R)-[(piperazine-1-sulfonyl)amino]propionateYield 91%

Reagents, catalysts & solvents 1

HCID 18626912Dioxane methylene chlorideSolvent

Procedure

Hydrogen chloride gas was bubbled through a solution of methyl 2-(R)-[(4-tert-butoxycarbonylpiperazine-1-sulfonyl)amino]propionate (3.6 g, 10.7 mmol) [prepared by proceeding as described in Example 2, but substituting 4-(5-chloropyridin-2-yloxy)piperidine and D-valine methyl ester with 1-tert-butoxycarbonyl-1,4-piperazine and D-alanine methyl ester, respectively] in 10% dioxane/methylene chloride (100 ml) for 10 min. The reaction was stirred at RT for 4 h and concentrated in vacuo to give methyl 2-(R)-[(piperazine-1-sulfonyl)amino]propionate (91%) as a white solid that was used without further purification.

Workup

  1. customprepared
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c0e4ef846394dbfa8219a1c04d5cd21
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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