Triethylamine → HCID 71581630, compound

HRID 530251Notes

Reaction equation

HRID 530251 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C@@:11]([C@@H:14]3[C@@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][C:15]3([CH3:22])[CH3:21])([OH:13])[CH3:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(N(CC)CC)C.[N:30]([Si](C)(C)C)=[C:31]=[O:32]>ClCCl>[OH:13][C@@:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH2:1][N:2]([C:31]([NH2:30])=[O:32])[CH2:3][CH2:4]2)([C@@H:14]1[C@@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][C:15]1([CH3:21])[CH3:22])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 117720122HCID 117720122, compound

Product 1

HCID 71581630HCID 71581630, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound of the crude product of Example 13c (28 mg, 0.1 mmol) in dichloromethane (2 mL) was added triethylamine (55 mg, 0.5 mmol) and isocyanatotrimethylsilane (47 mg, 0.4 mmol). The reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed with water, saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a yellow oil (15 mg). Mass spectrum (LC ESI +ve) m/z 345 (M+H+).

Workup

  1. washwashed with water, saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-108cee94b1854724ab95c7e8b994177b
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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