4-Methoxybenzyl alcohol → HCID 67138887, compound

HRID 1592043Notes

Reaction equation

HRID 1592043 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[S:12](=[O:14])(=[O:13])[NH:11][C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]O)=[CH:39][CH:38]=1.N(C([O-])=O)=NC([O-])=O>C1COCC1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[S:12](=[O:14])(=[O:13])[N:11]([CH2:41][C:40]3[CH:43]=[CH:44][C:37]([O:36][CH3:35])=[CH:38][CH:39]=3)[C:10](=[O:15])[CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 11776TriphenylphosphineHCID 51573101N-carboxylatoiminocarbamateHCID 58997410HCID 58997410, compound2×

Product 1

HCID 67138887HCID 67138887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Example 45, 5-(4-iodo-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (355.9 mg, 1.05 mmol) is dissolved in THF (20 mL) in a 40 mL capacity septum capped vial, and stirred under argon balloon. Triphenylphosphine (552 mg, 2.11 mmol) is added as a solid and stirred until dissolved, then 4-methyoxybenzyl alcohol (0.156 mL, 1.26 mmol) is added by syringe. The stirred reaction is cooled in an ice bath, and disopropyl azodicarboxylate (0.415 mL, 2.11 mmol) is added slow dropwise by syringe. After two h, the reaction is concentrated in vacuo and the residue is taken up in CH2Cl2. Chromatography on a 35 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 10:90 (EtOAc:hexane) to 30:70 over 15 min gives 5-(4-iodo-phenyl)-2-(4-methoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a white solid. 1H-NMR (300 MHz, CDCl3) 3.80 (s, 3H), 4.37 (s, 2H), 4.79 (s, 2H), 6.89 (d, J=7.5, 2H, aryl), 7.03 (d, J=7.5, 2H), 7.41 (d, J=7.5, 2H), 7.73 (d, J=7.5, 2H).

Workup

  1. customcapped vial
  2. stirringstirred
  3. dissolutionuntil dissolved
  4. customThe stirred reaction
  5. temperatureis cooled in an ice bath
  6. concentrationAfter two h, the reaction is concentrated in vacuo
  7. washChromatography on a 35 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 10:90 (EtOAc:hexane) to 30:70 over 15 min

Sources & evidence

ORD record
ord-a50c621fa9bb40babaddcee1160fcca1
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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