Hydrochloric Acid → HCID 67097251, compound

HRID 2078664Notes

Reaction equation

HRID 2078664 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:34][C@H:35]([OH:42])[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:48]([Si:52]([CH3:55])([CH3:54])Cl)([CH3:51])([CH3:50])[CH3:49].Cl>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH2:34][C@H:35]([O:42][Si:52]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:55])[CH3:54])[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:18]=2)=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67097389HCID 67097389, compound

Product 1

HCID 67097251HCID 67097251, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of methyl 4′-[2-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-(cyclohexyloxy)-4-biphenylcarboxylate in N,N-dimethylformamide were added imidazole and tert-butyldimethylchlorosilane at room temperature. After stirring at room temperature for 15 minutes and at 35° C. for 3.5 hours. The reaction mixture was poured into 0.05N hydrochloric acid at room temperature. The products were extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography to give methyl 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-pyridyl)ethyl]amino]ethyl]-3-(cyclohexyloxy)-4-biphenylcarboxylate (11.22 g).

Workup

  1. extractionThe products were extracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1ea94213174a48ae992f179b7feb534d
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

Loading…