Triphenylphosphine → 5-(S)-Aminomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]-oxazolidine-2-one

HRID 412495Notes

Reaction equation

HRID 412495 reaction equation
C(C1C(OC)=CC(OCCCC(O)=O)=CC=1OC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(CNC(CN2C3C(=CC=CC=3)C(C=O)=C2)=O)=CC=1.[N:61]([CH2:64][C@H:65]1[O:69][C:68](=[O:70])[N:67]([C:71]2[CH:76]=[CH:75][C:74]([S:77][C:78]([C:91]3[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=3)([C:85]3[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=3)[C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)=[C:73]([F:97])[CH:72]=2)[CH2:66]1)=[N+]=[N-].C([BH3-])#N.[Na+]>ClCCl.C1COCC1.N1C=CC=CC=1>[NH2:61][CH2:64][C@@H:65]1[O:69][C:68](=[O:70])[N:67]([C:71]2[CH:76]=[CH:75][C:74]([S:77][C:78]([C:79]3[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=3)([C:85]3[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=3)[C:91]3[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=3)=[C:73]([F:97])[CH:72]=2)[CH2:66]1

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 892769Aldehyde resinHCID 27584194-(4-Formyl-3,5-dimethoxyphenoxy)butanoic acidHCID 5003444Sodium cyanoborohydrideHCID 229662215-(S)-azidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 229662065-(S)-Aminomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]-oxazolidine-2-one

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropylcarbodiiimide (4.24 ml, 27.0 mmol) was added to 4-(4-formyl-3,5-dimethoxyphenoxy)butyric acid (13.19 g, 49.2 mmol) and pyridine (20 mL) in dichloromethane (190 mL), and the mixture was stirred at room temperature for 1 h. Tentagel S-NH2 resin (Rapp Polymere, 30.0 g, 12.3 mmol) was added, and the mixture agitated at room temperature overnight. Resulted BAL resin was filtered, washed liberally with methanol and dichloromethane and dried under vacuum. Triphenylphosphine (7.97 g, 0.0304 mol) was added to a mixture of above BAL aldehyde resin (50.9 g, 0.0209 mol) and 5-(S)-azidomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]oxazolidine-2-one (15.5 g, 30.4 mmol) in THF (200 ml) under nitrogen at r.t. (room temperature). The mixture was agitated at r.t. for 2 h and then heated at 75° C. for 16 h. The mixture was cooled to r.t., and 1 M sodium cyanoborohydride in THF (62.7 ml, 62.7 mmol) was added. The mixture was agitated for 8 h at r.t. The resin was filtered, washed liberally with methanol and dichloromethane and dried under vacuum.

Workup

  1. additionTentagel S-NH2 resin (Rapp Polymere, 30.0 g, 12.3 mmol) was added
  2. stirringthe mixture agitated at room temperature overnight
  3. filtrationResulted BAL resin was filtered
  4. washwashed liberally with methanol and dichloromethane
  5. customdried under vacuum
  6. stirringThe mixture was agitated at r.t. for 2 h
  7. temperatureheated at 75° C. for 16 h
  8. temperatureThe mixture was cooled to r.t.
  9. stirringThe mixture was agitated for 8 h at r.t
  10. filtrationThe resin was filtered
  11. washwashed liberally with methanol and dichloromethane
  12. customdried under vacuum

Sources & evidence

ORD record
ord-767c284800734b8caf03a2a9d8b1ee3f
Source dataset
uspto-grants-2003_05
Patent number
US06562844B2

Reaction notes

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