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

HRID 351889Notes

Reaction equation

HRID 351889 reaction equation
NC[C@@H]1OC(=O)N(C2C=CC(S(C)=O)=C(F)C=2)C1.[N:19]([CH2:22][C@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH2:37][CH3:38])=[O:36])=[C:31]([F:39])[CH:30]=2)[CH2:24]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[NH2:19][CH2:22][C@@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH2:37][CH3:38])=[O:36])=[C:31]([F:39])[CH:30]=2)[CH2:24]1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 229662005-(S)-aminomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-oneHCID 229662115-(S)-Azidomethyl-3-[4'-ethylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 229661995-(S)-Aminomethyl-3-[4'-ethylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Procedure

This compound was prepared analogously to the synthesis of 5-(S)-aminomethyl-3-[4′-methylsulfinyl-3′-fluorophenyl]oxazolidine-2-one from 5-(S)-azidomethyl-3-[4′-ethylsulfinyl-3′-fluorophenyl]oxazolidine-2-one (0.235 g, 0.752 mmol) and triphenylphosphine (0.207 g, 0.790 mmol). Yield 0.177 g (82%). MS (m/z): [M+H]+=287.

Sources & evidence

ORD record
ord-8261d14a8f4f41a595cdb5519077603f
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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