HCID 86695117, compound → HCID 86695261, compound

HRID 1504099Notes

Reaction equation

HRID 1504099 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[C:28]3[C:27]4[C@@H:26]([CH2:29][CH:30]=[O:31])[CH2:25][CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Br[Mg][CH2:34][CH3:35]>C1COCC1>[OH:31][C@@H:30]([CH2:34][CH3:35])[CH2:29][C@H:26]1[CH2:25][CH2:24][C:23]2[S:22][C:21]3[N:20]=[CH:19][N:18]=[C:17]([O:16][CH:13]4[CH2:14][CH2:15][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7])[CH2:11][CH2:12]4)[C:28]=3[C:27]1=2.[OH:31][C@H:30]([CH2:34][CH3:35])[CH2:29][C@H:26]1[CH2:25][CH2:24][C:23]2[S:22][C:21]3[N:20]=[CH:19][N:18]=[C:17]([O:16][CH:13]4[CH2:14][CH2:15][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7])[CH2:11][CH2:12]4)[C:28]=3[C:27]1=2

Participants

5

Reactant 2

HCID 86695117HCID 86695117, compoundHCID 178418443HCID 178418443, compound

Product 2

HCID 68115533HCID 68115533, compoundYield 56%HCID 86695261HCID 86695261, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-methyl-N-(4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (370 mg, 0.83 mmol, 1.00 equiv) in freshly distilled THF (15 mL) was added dropwise bromo(ethyl)magnesium (0.46 mL, 1.25 mmol, 1.50 equiv) at 0° C. under nitrogen. The resulting solution was stirred for 2 h at r.t and quenched by the addition of H2O. The mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to give 0.11 g (56%) of tert-butyl N-(4-[[(3R)-3-[(2S)-2-hydroxybutyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (195.1) as a light yellow oil and 0.16 g (81%) of tert-butyl N-(4-[[(3R)-3-[(2R)-2-hydroxybutyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (196.1) as a light yellow oil.

Workup

  1. customquenched by the addition of H2O
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-8e51c8128e224ea9b3b6c92bef942c2f
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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