1,4-Dioxane hydrochloride → HCID 67607604, compound

HRID 1965194Notes

Reaction equation

HRID 1965194 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]2[N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:15][CH2:16][CH:9]12)=O)(C)(C)C.[ClH:27].O1CCOCC1>C(Cl)Cl.C1(C)C=CC=CC=1>[ClH:27].[CH2:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:9]2[NH:8][CH2:12][CH:11]([OH:13])[CH:10]12)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochloride2×HCID 676073943-Hydroxy-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Product 1

HCID 67607604HCID 67607604, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of bicyclic alcohol 43 (6.5 g, 17.9 mmol) in DCM (20 mL) at 0° C. was added 4N HCl/1,4-dioxane (20 mL, 80 mmol) and the reaction mixture was slowly warming to ambient temperature. After 90 min, an additional portion of 4N HCl/1,4-dioxane (20 mL) was added. After 3 h, the reaction mixture was diluted with toluene and concentrated in vacuo. The crude 52 (HCl salt) was used in the next step without further purification. Mass spectrum, m/z [262.5] (M+H)+.

Workup

  1. waitAfter 3 h
  2. concentrationconcentrated in vacuo
  3. customThe crude 52 (HCl salt) was used in the next step without further purification

Sources & evidence

ORD record
ord-1a947cc43a1e4660910ef82df76e2308
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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