Imidazole → HCID 131735381, compound

HRID 629729Notes

Reaction equation

HRID 629729 reaction equation
[OH:1][CH2:2][C@H:3]1[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][C@@H:6]([CH:16]([OH:27])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[O:5][CH2:4]1.N1C=CN=C1.[Si:33](Cl)([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.C(Cl)Cl.CCCCCCC>[Si:33]([O:1][CH2:2][C@H:3]1[N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:7][C@@H:6]([CH:16]([OH:27])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[O:5][CH2:4]1)([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 131735382HCID 131735382, compound

Product 1

HCID 131735381HCID 131735381, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

A solution of intermediate tert-butyl (2S,5R)-5-(hydroxymethyl)-2-[1-hydroxy-2-(2-nitrophenyl)ethyl]morpholine-4-carboxylate and imidazole (3.2 eq.) in dry DMF (0.43 M) was treated with neat TBDPS-Cl (1.1 eq.) and the final solution stirred at room temperature for 48 h, diluted with DCM and heptane (excess) and concentrated. The residue was purified by automated silicagel flash chromatography system eluted with a gradient 10% to 50% EtOAc in hexanes, to afford title compound as white foam.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by automated silicagel flash chromatography system
  3. washeluted with a gradient 10% to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-383faafcdc5f4f2aa637e0396103c4be
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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