Imidazole → HCID 58109435, compound

HRID 2037485Notes

Reaction equation

HRID 2037485 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH2:21])=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.N1C=CN=C1.[CH3:33][C:34]([Si:37](Cl)([CH3:39])[CH3:38])([CH3:36])[CH3:35]>C(Cl)Cl>[Si:37]([O:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:15]=[CH:16][C:17]([CH:20]=[CH2:21])=[CH:18][CH:19]=2)[CH3:13])[CH2:7][CH2:6]1)([C:34]([CH3:36])([CH3:35])[CH3:33])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58109276HCID 58109276, compound

Product 1

HCID 58109435HCID 58109435, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-6-(3-hydroxypropyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (50 mg, 0.137 mmol) and imidazole (11.2 mg 0.165 mmol) in CH2Cl2 (10 mL) was added a solution of TBSCl (24.6 mg, 0.164 mmol) in CH2Cl2 (15 mL) dropwise at 0° C. The mixture was stirred overnight at rt. The mixture was filtered, and the solvent was evaporated to give (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (40 mg, 60%). 1H NMR (CDCl3): 0.02 (s, 6H), 0.87 (m, 9H), 1.23 (m, 1H), 1.52 (d, 3H), 1.62 (m, 1H), 1.98 (m, 2H), 2.14-2.38 (m, 3H), 2.97 (m, 1H), 3.58 (m, 2H), 5.28 (m, 1H), 5.71 (m, 1H), 6.68 (m, 1H), 6.88 (m, 1H), 7.16 (m, 1H), 7.22-7.38 (m, 7H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-50391b2a35954c148d60d704e3650e17
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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