Hydrochloric Acid → HCID 67103382, compound

HRID 2081139Notes

Reaction equation

HRID 2081139 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:11]([O:13][C@@H:14]1[CH2:18][C@@H:17]([C:19](=[O:35])[NH:20][C@:21]3([C:26](=[O:34])[NH:27][S:28]([CH:31]4[CH2:33][CH2:32]4)(=[O:30])=[O:29])[CH2:23][C@H:22]3[CH2:24][CH3:25])[N:16](C(OC(C)(C)C)=O)[CH2:15]1)=[O:12])[CH2:6]2.[ClH:43].O1CCOCC1>C(Cl)Cl>[ClH:1].[ClH:43].[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:11]([O:13][C@@H:14]1[CH2:18][C@@H:17]([C:19](=[O:35])[NH:20][C@:21]3([C:26](=[O:34])[NH:27][S:28]([CH:31]4[CH2:32][CH2:33]4)(=[O:30])=[O:29])[CH2:23][C@H:22]3[CH2:24][CH3:25])[NH:16][CH2:15]1)=[O:12])[CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57988422HCID 57988422, compound

Product 1

HCID 67103382HCID 67103382, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R,5S)-1-(tert-butoxycarbonyl)-5-((1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate (1.35 g, 2.16 mmol) in DCM (5 mL) was added 4 N HCl in dioxane (4.32 ml, 17.3 mmol). The reaction mixture was stirred at rt for 2 hours. The solvent was removed and the residue was suspended in ethyl ether (30 mL) and stirred for 30 min. The solid was collected by filtration to give (3R,5S)-5-((1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate dihydrochloride (1.10 g, 91%) as white solid. LCMS (APCI+): 525.2.

Workup

  1. customThe solvent was removed
  2. stirringstirred for 30 min
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-81a3ebef7349402090df8169b22675ad
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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