Hydrochloric Acid → HCID 86635056, compound

HRID 1924383Notes

Reaction equation

HRID 1924383 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C@@H:12]2[CH2:16][N:15](C(OC(C)(C)C)=O)[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:28].O1CCOCC1>CCOCC>[ClH:28].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][C@@H:12]2[CH2:16][NH:15][C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 86635056HCID 86635056, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0.22 M solution of 1-tert-butyl 2-methyl (2S,4S)-4-[((4-bromophenyl)sulfonyl)oxy]pyrrolidine-1,2-dicarboxylate (prepared as described in WO2006/119061) in Et2O at 0° C. was added dropwise a 4M solution of HCl in dioxane (25 eq.) and the resulting mixture was stirred at RT for 16 h, after which time a solid product was formed. The suspension was filtered and the filter cake was washed with cold Et2O. The solid product was dried in vacuo and the product used without further purification. MS (ES+) C12H14BrNO5S requires: 363. Found: 364, 365 (M+H+).

Workup

  1. customafter which time a solid product was formed
  2. filtrationThe suspension was filtered
  3. washthe filter cake was washed with cold Et2O
  4. customThe solid product was dried in vacuo
  5. customthe product used without further purification

Sources & evidence

ORD record
ord-c588239a3a0a4f31acc2582351aa7df7
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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