Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 68679084, compound

HRID 2242180Notes

Reaction equation

HRID 2242180 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][C:23](=[O:44])[CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH:24][C:23]([O:22][CH3:21])=[O:44])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 58516805(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

Product 1

HCID 68679084HCID 68679084, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of Example 1A (5.77 g, 0.0192 mol) in anhydrous dichloromethane (30 mL) was added methyl(triphenylphosphoranylidene)-acetate (8.22 g, 0.0246 mol) and the resulting solution heated to 40° C. for two days. The mixture was cooled, concentrated and purified by column chromatography (ethyl acetate/hexane, 4/6) to provide the titled compound (3.42 g). MS (ESI APCI) m/e 355 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 5.87 (m, 1 H), 4.41-4.78 (m, 4 H), 4.31 (d, 1 H), 3.74-3.78 (m, 2 H), 3.17 (t, 2 H), 3.04 (t, 1 H), 2.74-2.80 (d, 1 H), 1.40 (s, 9 H).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompurified by column chromatography (ethyl acetate/hexane, 4/6)

Sources & evidence

ORD record
ord-d5d31f91d9d348f7b7adbeb1e68c1f69
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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