Trifluoroacetic acid → 5-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one

HRID 1979276Notes

Reaction equation

HRID 1979276 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:11]([F:35])[CH:10]=2)[CH2:4]1.C([SiH](C(C)C)C(C)C)(C)C.F[C:47](F)(F)[C:48](O)=[O:49]>ClCCl>[C:48]([NH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[C:11]([F:35])[CH:10]=2)[CH2:4]1)(=[O:49])[CH3:47]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 229662065-(S)-Aminomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 229661975-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BAL resin immobilized 5-(S)-Aminomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]-oxazolidine-2-one (5.00 g, 2.05 mmol) was suspended in 5% trifluoroacetic acid and 2.5% triisopropylsilane in dichloromethane (50 mL), and the mixture was agitated for 1 h. The resin was filtered and the procedure repeated with fresh 5% trifluoroacetic acid and 2.5% triisopropylsilane in dichloromethane (50 mL) for another 30 minutes. The resin was filtered and washed liberally with dichloromethane. Resulted thiol resin was immediately suspended in a mixture of acetic anhydride (20 mL) and pyridine (30 mL) in DCM (50 mL), and the mixture was agitated overnight at r.t. The resin was filtered, washed liberally with dichloromethane and dried under vacuum.

Workup

  1. filtrationThe resin was filtered
  2. filtrationThe resin was filtered
  3. washwashed liberally with dichloromethane
  4. additionResulted thiol resin was immediately suspended in a mixture of acetic anhydride (20 mL) and pyridine (30 mL) in DCM (50 mL)
  5. filtrationThe resin was filtered
  6. washwashed liberally with dichloromethane
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6a4c80e098ad41cd902dd672d6f001a6
Source dataset
uspto-grants-2001_05
Patent number
US06239152B1

Reaction notes

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