Dichloromethane → HCID 178463344, compound

HRID 1944748Notes

Reaction equation

HRID 1944748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C@@H:21]3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:19])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH:39][CH2:40][CH3:41].C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][C@@H:21]3[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:19])[CH2:14][CH2:13]2)(=[O:9])=[O:10])=[CH:4][C:3]=1[NH:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 178463345HCID 178463345, compound

Product 1

HCID 178463344HCID 178463344, compoundYield 488.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-tert-Butyl 4-(trans-4-(4-chloro-3-(ethylamino)phenylsulfonamido)cyclo-hexanecarbonyl)-3-phenylpiperazine-1-carboxylate (Example 1, 77 mg, 0.127 mmol) was stirred in 20% v/v TFA/DCM overnight. The reaction was dilutee with DCM and water and the pH was adjusted to 13 with 1N NaOH. The layers were separated, and the organic layer was concentrated and chromatographed on reverse phase Phenomenex Gemini Axia C18 30×100 mm column using a gradient of 15-100% AcCN in water containing 5 mM ammonium hydroxide. The product was lyophilized to yield the title compound (31.5 mg, 0.62 mmol). MS MH+ 505.4.

Workup

  1. customThe layers were separated
  2. concentrationthe organic layer was concentrated
  3. customchromatographed on reverse phase Phenomenex Gemini Axia C18 30×100 mm column

Sources & evidence

ORD record
ord-ae3d8e396e9c4ebe999c37e02be6e859
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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