Cyclopropanecarbonyl chloride → HCID 9933614, compound

HRID 2287419Notes

Reaction equation

HRID 2287419 reaction equation
C1([C:4](Cl)=[O:5])CC1.[F:7][C:8]1[CH:9]=[C:10]([N:22]2[CH2:26][C@H:25]([CH2:27][NH2:28])[O:24][C:23]2=[O:29])[CH:11]=[CH:12][C:13]=1[CH:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]1.CO.[CH:32]([Cl:35])(Cl)[Cl:33]>>[Cl:33][CH:32]([Cl:35])[C:4]([NH:28][CH2:27][C@@H:25]1[O:24][C:23](=[O:29])[N:22]([C:10]2[CH:11]=[CH:12][C:13]([CH:14]3[CH2:15][CH2:16][S:17](=[O:20])(=[O:21])[CH2:18][CH2:19]3)=[C:8]([F:7])[CH:9]=2)[CH2:26]1)=[O:5]

Participants

4

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 21584188Chloroform methanolHCID 54349937(5S)-(-)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone

Product 1

HCID 9933614HCID 9933614, compound

Procedure

Following the general procedure of EXAMPLE 3, and making non-critical variations but substituting dichloroacetyl chloride for cyclopropanecarbonyl chloride and (5S)-(-)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone (EXAMPLE 5, Step 1) for (5S)-3-[3-fluoro-4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone and chromatographing the crude product with methanol/chloroform (2/98), the title compound is obtained, mp 136-137° C. (dec.).

Sources & evidence

ORD record
ord-68a93b4e4e8a426b89e83552557c2511
Source dataset
uspto-grants-2000_07
Patent number
US06083967

Reaction notes

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