HCID 57527002, compound → HCID 68878196, compound

HRID 1452567Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][CH:20]([CH2:22][N:23]=[N+]=[N-])[O:19][C:18]2=[O:26])[CH:5]=[C:6]([F:16])[C:7]=1[N:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[CH2:10][CH2:9]1.N(C[C@@H]1OC(=O)N(C2C=C(F)C(N3CCS(=O)(=O)CC3)=C(F)C=2)C1)=[N+]=[N-]>>[O:15]=[S:11]1(=[O:14])[CH2:10][CH2:9][N:8]([C:7]2[C:6]([F:16])=[CH:5][C:4]([N:17]3[CH2:21][C@@H:20]([CH2:22][NH2:23])[O:19][C:18]3=[O:26])=[CH:3][C:2]=2[F:1])[CH2:13][CH2:12]1

Participants

Reactant 2

HCID 57527002HCID 57527002, compound

HCID 76556212HCID 76556212, compound

Product 1

HCID 68878196HCID 68878196, compoundYield 85.2%

Procedure

A suspension of (5R) 3-[3,5-difluoro-4-(1,1-dioxo-4-thiomorpholinyl)phenyl]-5-(azidomethyl)-oxazolidin-2-one (Intermediate 10) (0.82 g, 2.11 mmol) and polystyrene triphenylphosphine (5.6 g, 8.5 mmol) was reacted as described for Example 9 to give the intermediate amine, (5R)-3-[4-(1,1-Dioxo-4-thiomorpholinyl)-3,5-difluorophenyl]-5-(aminomethyl)-oxazolidin-2-one (0.65 g), which was used directly for the next step. This amine (0.63 g, 1.75 mmol) was reacted with diisopropylethylamine (0.9 ml, 5.2 mmol) and α,α-dichloroacetone tosylhydrazone (0.77 g, 2.62 mmol) as described for Example 3. Chromatography on silica gel eluting with 5% methanol in dichloromethane gave the title compound (350 mg).

Workup

customwas reacted

Sources & evidence

ORD record: ord-22be67ceb6ad4deab64e593f499929d5
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473699B2

Reaction notes

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