Iodoethane → HCID 58452518, compound

HRID 70684Notes

Reaction equation

HRID 70684 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([O:30]C)[N:24]=2)=[CH:16][C@@H:17]2[NH:21][C:20](=[O:22])[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[CH2:32](I)[CH3:33]>>[Cl:29][C:26]1[C:25](=[O:30])[NH:24][C:23]([CH:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:32][CH3:33])=[CH:14][CH:13]=2)[CH2:16][C@H:17]2[CH2:18][CH2:19][C:20](=[O:22])[NH:21]2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 67398390HCID 67398390, compound

Product 1

HCID 58452518HCID 58452518, compound

Procedure

An (R,S) mixture of the title compound was obtained as a colorless amorphous (240 mg) by performing substantially the same reaction as in Examples 1-16(2)(3) and 4-209 and 4-210(2)(3) sequentially except for using (5R)-5-[2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one obtained in Example 4-48(1) and using ethyl iodide in place of methyl iodide. This was separated by chiral HPLC (CHIRALCEL OD-H, 40° C., flow rate: 7 mL/min, ethanol:hexane=0:100) to give one diastereomer (A) of the title compound as a colorless amorphous (38 mg) and the other diastereomer (B) of the title compound as a colorless amorphous (35 mg).

Workup

  1. customwas obtained as a colorless amorphous (240 mg)
  2. customthe same reaction as in Examples 1-16(2)(3) and 4-209 and 4-210(2)(3) sequentially except
  3. customThis was separated by chiral HPLC (CHIRALCEL OD-H, 40° C., flow rate: 7 mL/min, ethanol:hexane=0:100)

Sources & evidence

ORD record
ord-95635fd9c6434c12b531516aee5e558d
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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