Potassium Carbonate → HCID 68700548, compound

HRID 643906Notes

Reaction equation

HRID 643906 reaction equation
[CH2:1]([O:8][C:9]1[C:10](N2S(=O)(=O)NC(=O)C2)=[CH:11][C:12]2[CH2:13][CH2:14][CH:15]([OH:19])[CH2:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C([N:40]2[S:44](=[O:46])(=[O:45])[NH:43][C:42](=[O:47])[CH2:41]2)=CC2CCC(O)CC=2C=1.Cl[CH2:49][O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([C:53]2[C:52]([CH2:51][O:50][CH2:49][N:43]3[C:42](=[O:47])[CH2:41][NH:40][S:44]3(=[O:45])=[O:46])=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:11][C:12]2[CH2:13][CH2:14][CH:15]([OH:19])[CH2:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl etherHCID 17751436HCID 17751436, compoundHCID 66750740HCID 66750740, compound

Product 1

HCID 68700548HCID 68700548, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(3-benzyloxy-6-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (158 mg, 0.40 mmol), intermediate from Example 45, chloromethoxymethylbenzene (0.068 mL, 0.49 mmol) and potassium carbonate (110 mg, 0.80 mmol) in DMF (4 mL) is stirred at RT for 18 h. The mixture is partitioned between EtOAc and 1 N HCl solution. The organic extract is dried with MgSO4 and concentrated. The residue is purified by chromatography to give the title compound as an oil: (M+NH4)+=526.

Workup

  1. customThe mixture is partitioned between EtOAc and 1 N HCl solution
  2. extractionThe organic extract
  3. dry with materialis dried with MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-719130c62d6548d9a5977d7b8c675b83
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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