Triphenylphosphine → (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester

HRID 987325Notes

Reaction equation

HRID 987325 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:18]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH2:54]([O:56][C@@H:57]([CH2:61][C:62]1[CH:67]=[CH:66][C:65](O)=[CH:64][CH:63]=1)[C:58]([OH:60])=[O:59])[CH3:55]>ClCCl>[CH2:17]([O:60][C:58](=[O:59])[C@@H:57]([O:56][CH2:54][CH3:55])[CH2:61][C:62]1[CH:67]=[CH:66][C:65]([O:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([S:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:9][CH:10]=2)=[CH:64][CH:63]=1)[CH3:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9837207(2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acidHCID 13567669HCID 13567669, compound

Product 1

HCID 54503267(S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-[4-(Phenylsulfanyl)phenyl]-1-ethanol (1.22 g; 5.12 mmole), triphenylphosphine (2 g; 7.6 mmole) and 1,1′-(azodicarbonyl)dipiperidine were dissolved in dichloromethane (15 ml). After 10 minutes a solution of (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid (described in Example 40b) in dichloromethane (15 ml) was added and the reaction mixture was stirred over night at room temperature. The solid material was filtered off and the solvent evaporated. Chromatography of the residue on siliga gel using ethyl acetate:petroleum ether (40-60° C.), (1:99, 5:95 and 10:90) gave 1.24 g (yield 47%) of (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester.

Workup

  1. filtrationThe solid material was filtered off
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-2622edb8072644899376e8580cfaa27d
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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