Ninhydrin → 5-(S)-Acetamidomethyl-3-[4'-dimethoxymethyl-3'-fluorophenyl]-oxazolidine-2-one

HRID 412490Notes

Reaction equation

HRID 412490 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.ClCCl.[NH2:17][CH2:18][C@@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([O:34][CH3:35])[O:32][CH3:33])=[C:27]([F:36])[CH:26]=2)[CH2:20]1.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>>[C:1]([NH:17][CH2:18][C@@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([O:32][CH3:33])[O:34][CH3:35])=[C:27]([F:36])[CH:26]=2)[CH2:20]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 10236NinhydrinHCID 20443498acetic anhydride pyridine CH2Cl2HCID 229773175-(S)-Aminomethyl-3-[4'-dimethoxymethyl-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 229773135-(S)-Acetamidomethyl-3-[4'-dimethoxymethyl-3'-fluorophenyl]-oxazolidine-2-one

Procedure

Acetic anhydride-pyridine-dichloromethane solution (1 to 1.5 to 3, 4 mL) was added to BAL resin immobilized 5-(S)-aminomethyl-3-[4′-dimethoxymethyl-3′-fluorophenyl]-oxazolidine-2-one, and the mixture was agitated for ca. 2 h (until negative ninhydrine test indicated completion of the acylation). The resin was filtered, washed liberally with methanol and dichloromethane and dried under vacuum.

Workup

  1. filtrationThe resin was filtered
  2. washwashed liberally with methanol and dichloromethane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-939e58bc94b943b5b8899cb6c62f791f
Source dataset
uspto-grants-2003_05
Patent number
US06562844B2

Reaction notes

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