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

HRID 1276446Notes

Reaction equation

HRID 1276446 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][NH:16][CH2:17][CH:18]=3)=[C:9]([F:19])[CH:8]=2)[CH2:5][C@H:4]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:3]1.O=C1N(C2C=CC(C3CCNCC3)=CC=2)CC(CCC(N)=O)O1.[C:48]([O:51][CH2:52][C:53](Cl)=[O:54])(=[O:50])[CH3:49].C(OCC(Cl)=O)C1C=CC=CC=1>>[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:53](=[O:54])[CH2:52][O:51][C:48](=[O:50])[CH3:49])[CH2:17][CH:18]=3)=[C:9]([F:19])[CH:8]=2)[CH2:5][C@H:4]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:3]1

Participants

5

Reactant 4

HCID 26297Acetoxyacetyl chlorideHCID 177085Benzyloxyacetyl chlorideHCID 11559039(S)-(-)-N-[[2-Oxo-3-[4-(3,6-dihydro-2H-pyridin-4-yl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamideHCID 86756146[2-Oxo-3-[4-(4-piperidinyl)phenyl]-5-oxazolidinyl]methyl acetamide

Product 1

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

Procedure

Following the general procedure of EXAMPLE 18, and making non-critical variations but substituting (S)-(-)-N-[[2-oxo-3-[4-(3,6-dihydro-2H-pyridin-4-yl)-3-fluorophenyl]-5-oxazolidinyllmethyl]acetamide (EXAMPLE 38) for (S)-(-)-N-[[2-oxo-3-[4-(4-piperidinyl)phenyl]-5-oxazolidinyl]methyl acetamide and acetoxyacetyl chloride for benzyloxyacetyl chloride, the title compound is obtained, mp 188-191° C.

Sources & evidence

ORD record
ord-6c627cdb15954e55890c34cf5e2ce003
Source dataset
uspto-grants-2000_12
Patent number
US06166056

Reaction notes

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