(S)-(-)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide → (S)-(-)-N-[[3-[4-[1-(Hydroxyacetyl)-3,6-dihydro-2H-pyridin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1740167Notes

Reaction equation

[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH2:14][CH2:15][N:16]([C:19](=[O:25])[CH2:20][O:21]C(=O)C)[CH2:17][CH:18]=3)=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:3]1.O=C1N(C2C=CC(C3CCN(C(=O)COC(=O)C)CC=3)=C(F)C=2)C[C@H](CNC(=O)C)O1>>[OH:21][CH2:20][C:19]([N:16]1[CH2:17][CH:18]=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([N:6]3[CH2:5][C@H:4]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:3][C:2]3=[O:1])=[CH:12][CH:11]=2)[CH2:14][CH2:15]1)=[O:25]

Participants

Reactant 2

HCID 18684835(S)-(-)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide

HCID 54460068(S)-(-)-N-[[2-Oxo-3-[4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 54513710(S)-(-)-N-[[3-[4-[1-(Hydroxyacetyl)-3,6-dihydro-2H-pyridin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Procedure

Following the general procedure of EXAMPLE 40, and making non-critical variations but substituting (S)-(-)-N-[[2-oxo-3-[4-[1-(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 59) for (S)-(-)-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide, the title compound is obtained, HRMS (FAB) calcd for C19H23N3O5 +H: 374.1716. Found: 374.1713.

Sources & evidence

ORD record: ord-594030988829420e8be7536563443288
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968962

Reaction notes

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