Triphenylphosphine → HCID 67138359, compound

HRID 1591966Notes

Reaction equation

HRID 1591966 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][NH:8][S:7]1(=[O:13])=[O:12].[C:20]([O:24][C:25](=[O:35])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33]O)=[CH:29][CH:28]=1)([CH3:23])([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:20]([O:24][C:25](=[O:35])[NH:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:33][N:8]2[CH2:9][C:10](=[O:11])[N:6]([CH2:5][C:4]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:3]=3[O:2][CH3:1])[S:7]2(=[O:13])=[O:12])=[CH:31][CH:32]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10242688Boc-4-aminobenzylalcoholHCID 66751042HCID 66751042, compound

Product 1

HCID 67138359HCID 67138359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title B compound, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (98 mg, 0.34 mmol) and (4-hydroxymethylphenyl)carbamic acid t-butyl ester (153 mg, 0.68 mmol) and triphenylphosphine (180 mg, 0.68 mmol) are dissolved in THF (10 mL) with stirring under argon atmosphere. The reaction is cooled in an ice/water bath and diethyl azodicarboxylate (0.107 mL, 0.68 mmol) dissolved in THF (0.107 mL) is added dropwise. After 16 h, the solvent is evaporated and the residue is taken up in a minimal amount of CH2Cl2 and chromatographed on silica gel with a gradient from 1 to 5% EtOAc in CH2Cl2 over 15 min to give {4-[5-(2,4-dimethoxybenzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-phenyl}-carbamic acid t-butyl ester as an oil: [M+NH4]+=509.

Workup

  1. temperatureThe reaction is cooled in an ice/water bath
  2. additionis added dropwise
  3. customthe solvent is evaporated
  4. customchromatographed on silica gel with a gradient from 1 to 5% EtOAc in CH2Cl2 over 15 min

Sources & evidence

ORD record
ord-302720bb3dc047c78112d4019be7f9d3
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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