Water → HCID 57527013, compound

HRID 1452605Notes

Reaction equation

HRID 1452605 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([N:16]2[CH2:20][C@H:19]([CH2:21][N:22]3[CH:26]=[C:25]([CH3:27])[N:24]=[N:23]3)[O:18][C:17]2=[O:28])[CH:6]=[C:7]([F:15])[C:8]=1[C:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=1.N1C=CC=CC=1.[CH3:35][C:36]1([CH3:44])[O:40][C@H:39]([C:41](Cl)=[O:42])[CH2:38][O:37]1.O>ClCCl>[CH3:35][C:36]1([CH3:44])[O:40][C@H:39]([C:41]([N:12]2[CH2:11][CH:10]=[C:9]([C:8]3[C:7]([F:15])=[CH:6][C:5]([N:16]4[CH2:20][C@H:19]([CH2:21][N:22]5[CH:26]=[C:25]([CH3:27])[N:24]=[N:23]5)[O:18][C:17]4=[O:28])=[CH:4][C:3]=3[F:2])[CH2:14][CH2:13]2)=[O:42])[CH2:38][O:37]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10374773HCID 10374773, compoundHCID 68879337HCID 68879337, compound2×

Product 1

HCID 57527013HCID 57527013, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(5R)-3-[3,5-Difluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one hydrochloride (Intermediate 53) (1.13 g, 2.75 mmol) was suspended in dichloromethane (20 ml). Pyridine (2.22 ml, 27.50 mmol) was added and the solution was cooled to 0° C. A solution of (4S)-2,2-dimethyl-1,3-dioxolane-4-carbonyl chloride (WO 01/81350, 0.89 g, 5.43 mmol) in dichloromethane (10 ml) was added. After 2 hours, the solution was poured into water, the organic phase was washed with brine, dried over magnesium sulfate and concentrated under vacuum. Chromatography on silica gel with ethyl acetate gave 542 mg of the title product.

Workup

  1. washthe organic phase was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d526dc98039c49b0baa33d41bc63cb28
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

Loading…