Triphenylphosphine → HCID 67139934, compound

HRID 1592007Notes

Reaction equation

HRID 1592007 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].[CH2:20]([O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35]O)=[CH:31][CH:30]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:20]([O:27][C:28](=[O:37])[C:29]1[CH:30]=[CH:31][C:32]([CH2:35][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:33][CH:34]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15650225Benzyl 4-(hydroxymethyl)benzoateHCID 66751042HCID 66751042, compound

Product 1

HCID 67139934HCID 67139934, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of the title B compound in Example 9, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (2.0 g, 7.0 mmol) and 4-hydroxymethyl-benzoic acid benzyl ester (2.54 g, 10.5 mmol) in THF (50 mL) is added triphenylphosphine (3.67 g, 14 mmol) and the mixture is stirred until dissolved. The reaction is cooled to 0° C. and diethyl azodicarboxylate (2.20 mL, 14 mmol) dissolved in THF (20 mL) is added dropwise. The reaction is stirred for 16 h, while allowing to warm to RT, then concentrated. The residue is taken up in CH2Cl2, and chromatographed in two portions on a 110 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 0:100 (EtOAc:hexane) to 5:95 over 10 min. Fractions containing product are combined and concentrated to yield 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid benzyl ester as a white solid.

Workup

  1. dissolutionuntil dissolved
  2. additionis added dropwise
  3. stirringThe reaction is stirred for 16 h
  4. temperatureto warm to RT
  5. concentrationconcentrated
  6. customchromatographed in two portions on a 110 g silica gel RediSep column (Isco, Inc.) with a 30 mL/min gradient elution of 0:100 (EtOAc:hexane) to 5:95 over 10 min
  7. additionFractions containing product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5a3ce1d0c0bc44dbba17bf51d08304c9
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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