Water → HCID 59485747, compound

HRID 1972293Notes

Reaction equation

HRID 1972293 reaction equation
[Cl:1][C:2]1[CH:60]=[CH:59][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][O:27]C5CCCCO5)[CH:19]=4)[CH2:16][N:15]([CH2:34][CH2:35][S:36]([N:39](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)(=[O:38])=[O:37])[C:14]3=[O:58])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][OH:27])[CH:19]=4)[CH2:16][N:15]([CH2:34][CH2:35][S:36]([NH2:39])(=[O:37])=[O:38])[C:14]3=[O:58])=[CH:9][CH:8]=2)=[CH:59][CH:60]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59485926HCID 59485926, compound

Product 1

HCID 59485747HCID 59485747, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-((4S)-3-(4-(4-chlorophenoxy)phenyl)-2-oxo-4-(3-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)phenyl)imidazolidin-1-yl)-N,N-bis(4-methoxybenzyl)-ethane-sulfonamide (40 mg, 0.046 mmol) in TFA (1 mL) is stirred at room temperature for 2 h and is then concentrated. The residue is dissolved in MeOH (1 mL) and NaOH (0.09 mmol, 1M aqueous solution) is added. The mixture is stirred at room temperature for 14 h and is treated with water (3 mL) and extracted with EtOAc (3×3 ml). The combined organic layers are concentrated and purified by flash column chromatography (silica gel, 0-100% EtOAc/hexane) to provide the title compound as a white solid (20 mg, 81%). 1H NMR (CDCl3, 400 MHz) δ 7.21-7.28 (m, 5H), 6.81-6.97 (m, 7H), 5.67 (s, 2H), 5.16 (dd, J=9.2, 6.8 Hz, 1H), 3.98-4.08 (m, 2H), 3.92 (m, 3H), 3.75-3.80 (m, 2H), 3.26-3.41 (m, 3H), 2.37 (br s, 1H); HPLC-MS calculated for C25H26ClN3O6S (M+H+) 532.1, found 532.1.

Workup

  1. concentrationis then concentrated
  2. dissolutionThe residue is dissolved in MeOH (1 mL)
  3. extractionextracted with EtOAc (3×3 ml)
  4. concentrationThe combined organic layers are concentrated
  5. custompurified by flash column chromatography (silica gel, 0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-1fa65a1eef014a02bd5a48e375ff6bc3
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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