Sodium hydride → HCID 68115366, compound

HRID 1503897Notes

Reaction equation

HRID 1503897 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:19]1[N:20]=[CH:21][N:22]=[C:23]2[C:30]=1[C:29]1[C@H:28]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:27][CH2:26][C:25]=1[S:24]2>O1CCCC1>[C:11]([O:10][C:9]([NH:8][CH:5]1[CH2:6][CH2:7][CH:2]([O:1][C:19]2[N:20]=[CH:21][N:22]=[C:23]3[C:30]=2[C:29]2[C@H:28]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:27][CH2:26][C:25]=2[S:24]3)[CH2:3][CH2:4]1)=[O:15])([CH3:12])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanolHCID 86695083HCID 86695083, compound

Product 1

HCID 68115366HCID 68115366, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl N-(4-hydroxycyclohexyl)carbamate (412 mg, 1.91 mmol, 1.10 equiv) in freshly distilled tetrahydrofuran (10 mL) was treated with sodium hydride (60% dispersion in mineral oil, 280 mg, 4.00 equiv) for 1 h at room temperature under nitrogen. To this mixture was then added a solution of 16.3 (510 mg, 1.72 mmol, 1.00 equiv) in dry tetrahydrofuran (5 mL) via syringe. After stirring overnight at room temperature, the reaction was then quenched with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine and dried over sodium sulfate. After filtration and concentration under reduced pressure, the residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1:2) and purified to afford ethyl 2-[(3S)-12-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetate (16.4, 400 mg, 49%) as a yellow oil.

Workup

  1. customthe reaction was then quenched with water
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. custompurified

Sources & evidence

ORD record
ord-51a4d12785dc432dbaa7b64198c4220a
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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