Triphenylphosphine → HCID 54139683, compound

HRID 987314Notes

Reaction equation

HRID 987314 reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:48](=[O:52])[CH:49]([CH3:51])[CH3:50])=[CH:43][CH:42]=1.[CH2:53]([O:55][C:56](=[O:69])[C@@H:57]([O:66][CH2:67][CH3:68])[CH2:58][C:59]1[CH:64]=[CH:63][C:62](O)=[CH:61][CH:60]=1)[CH3:54]>ClCCl>[CH2:53]([O:55][C:56](=[O:69])[C@@H:57]([O:66][CH2:67][CH3:68])[CH2:58][C:59]1[CH:64]=[CH:63][C:62]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([NH:47][C:48](=[O:52])[CH:49]([CH3:50])[CH3:51])=[CH:43][CH:42]=2)=[CH:61][CH:60]=1)[CH3:54]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 22988433HCID 22988433, compound2×

Product 1

HCID 54139683HCID 54139683, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Azodicarbonyl dipiperidine (0.99 g; 3.93 mmole) and triphenylphosphine (1.03 g; 3.93 mmole) were added to a solution of N-[4-(2-hydroxyethyl)phenyl]isobutyramide (described in Example 68a) (0.79 g; 3.93 mmole) and (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (described in Example 40h) (0.78 g; 3.27 mmole) in dry dichloromethane (25 ml). After stirring at room temperature over night more N-[4-(2-hydroxyethyl)phenyl]isobutyramide, azodicarbonyl dipiperidine (0.16 g; 0.65 mmole) and triphenylphosphine (0.17 g; 0.65 mmole) were added. After stirring for 24 hours the reaction mixture was filtered and the solvent was evaporated in vacuo. Purification by chromatography on silica gel using heptane:ethyl acetate (2:1) as eluant gave 1.22 g (yield 87%) of (S)-2-ethoxy-3-{4-[2-(4-isobutyrylaminophenyl)ethoxy]phenyl}propanoic acid ethyl ester.

Workup

  1. additionwere added
  2. filtrationwas filtered
  3. customthe solvent was evaporated in vacuo
  4. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-ea6d42ee3f8c46fc9012ab5e45d04d3e
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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