Triphenylphosphine → (S,Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propanoate

HRID 517582Notes

Reaction equation

HRID 517582 reaction equation
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:31]O)[C:27]([O:29][CH3:30])=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(OCC)(=O)C>[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:31][N:11]1[C:10](=[O:15])/[C:9](=[CH:8]/[C:7]2[CH:16]=[CH:17][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)/[S:13][C:12]1=[O:14])[C:27]([O:29][CH3:30])=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 7019177N-Boc-L-serine methyl ester

Product 1

HCID 86724394(S,Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)propanoateYield 99.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 2 (285 mg, 1.15 mmol), (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate (251 mg, 1.15 mmol) and triphenylphosphine (452 mg, 1.72 mmol) were dissolved in 11 mL of anhydrous THF, and stirred at room temperature for 5 min. DIAD (338 μL, 1.72 mmol) was added to the reaction mixture and then stirred overnight at 45° C. The reaction mixture was diluted with ethyl acetate and washed with sat'd NH4Cl aqueous solution. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (30% ethyl acetate in hexanes) to afford compound 21d (99.5%, 517 mg) as a white solid.

Workup

  1. stirringstirred overnight at 45° C
  2. washwashed with sat'd NH4Cl aqueous solution
  3. customThe organic layer was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica column chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2f702ee5511b41dab1f5cfce1f28d1b4
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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