Methanol → HCID 10217340, compound

HRID 1268989Notes

Reaction equation

HRID 1268989 reaction equation
[O:1]=[S:2]1(=[O:31])[CH2:7][CH:6]=[C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][N:21]4[CH:25]=[C:24]([CH2:26][CH2:27]O)[N:23]=[N:22]4)[O:17][C:16]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1.S(Cl)([Cl:34])=O.CO>ClCCl>[O:1]=[S:2]1(=[O:31])[CH2:7][CH:6]=[C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][N:21]4[CH:25]=[C:24]([CH2:26][CH2:27][Cl:34])[N:23]=[N:22]4)[O:17][C:16]3=[O:29])=[CH:10][C:9]=2[F:30])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 10217041HCID 10217041, compound

Product 1

HCID 10217340HCID 10217340, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[4-(2-hydroxyethyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 51) (300 mg, 0.66 mmol) was reacted with thionylchloride (78.5 mg, 1.98 mmol) as described for Example 52. Chromatography on silica gel with 2.5% methanol in dichloromethane gave the title compound (285 mg).

Sources & evidence

ORD record
ord-f921e63adfb24b7789ea0eed7b728bc3
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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