Triethylamine → HCID 25007407, compound

HRID 252424Notes

Reaction equation

HRID 252424 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH:7]3[O:12][CH:10]([CH2:11][C:4]=2[C:3]=1[C:13]([CH:15]1[CH2:18][CH2:17][CH2:16]1)=[O:14])[CH2:9][CH2:8]3.C(N(CC)CC)C.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[CH3:38][C:39]([NH2:43])([CH2:41][CH3:42])[CH3:40]>O1CCCC1>[CH:15]1([C:13]([C:3]2[C:4]3[CH2:11][CH:10]4[O:12][CH:7]([CH2:8][CH2:9]4)[C:5]=3[S:6][C:2]=2[NH:1][C:30]([NH:43][C:39]([CH3:40])([CH3:38])[CH2:41][CH3:42])=[O:36])=[O:14])[CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 689862-Butanamine, 2-methyl-HCID 94429TriphosgeneHCID 66846392HCID 66846392, compound

Product 1

HCID 25007407HCID 25007407, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 20-mL scintillation vial containing a magnetic stir bar were added the product from Example 8A (263 mg, 1.00 mmol), anhydrous tetrahydrofuran (8 mL), and triethylamine (354 mg, 488 μL, 3.50 mmol), followed by drop-wise addition of a solution of triphosgene (0.35 mmol) in anhydrous tetrahydrofuran (2 mL). The resulting mixture was stirred at room temperature for 2 hours. A 2-mL aliquot of the mixture was removed and placed in a separate scintillation vial containing a magnetic stir bar and neat 2-methylbutan-2-amine (87 mg, 1.00 mmol) was added. The resulting mixture was stirred at room temperature overnight. The solvent and volatiles were removed by rotary evaporatory and the product was purified by flash chromatography (silica gel: 25% ethyl acetate, 75% hexanes—product Rf˜0.3) to give 42 mg (56%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 0.79 (t, J=7.4Hz, 3H), 1.22 (s, 3H), 1.23 (s, 3H), 1.54-2.30 (m, 12H), 3.13-3.20 (m, 2H), 3.67-3.77 (m, 1H), 4.67-4.70 (m, 1H), 4.95-4.97 (m, 1H), 7.68 (s, 1H), 11.39 (br s, 1H); MS (ESI+) m/z 377 (M+H)+. Anal. calcd. for C20H28N2O3S: C, 63.80; H, 7.50; N; 7.50. Found: C, 63.65; H, 7.86; N, 7.37.

Workup

  1. additionTo a 20-mL scintillation vial containing a magnetic stir bar
  2. customA 2-mL aliquot of the mixture was removed
  3. additioncontaining a magnetic stir bar
  4. stirringThe resulting mixture was stirred at room temperature overnight
  5. customThe solvent and volatiles were removed by rotary evaporatory
  6. customthe product was purified by flash chromatography (silica gel: 25% ethyl acetate, 75% hexanes—product Rf˜0.3)

Sources & evidence

ORD record
ord-a223a2b6227d4172b2809a7c6849bd83
Source dataset
uspto-grants-2011_01
Patent number
US07868038B2

Reaction notes

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