Triethylamine → HCID 178453655, compound

HRID 1159362Notes

Reaction equation

HRID 1159362 reaction equation
CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C[N:17]([CH2:25][C@H:26]1[CH2:29][C@H:28]([O:30]C2C=CC(CN3CCCC3)=CC=2)[CH2:27]1)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].NC[C@@H]1C[C@H](O)C1.CCN(CC)CC>C1COCC1>[OH:30][C@@H:28]1[CH2:29][C@H:26]([CH2:25][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:27]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178484147HCID 178484147, compoundHCID 178511298HCID 178511298, compound

Product 1

HCID 178453655HCID 178453655, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Boc)2O (4.42 g, 0.02 mol) was added to a solution of intermediate 9, cis-3-(aminomethyl)cyclobutanol (1.95 g, 0.019 mol) and Et3N (5.6 mL, 0.039 mol) in 20 mL absolute THF under stirring. The mixture was stirred at room temperature for 30 min, evaporated, and coevaporated with CCl4. The residue was recrystallized form ether to give the title compound (3 g, 77%) as yellow crystals. 1H NMR-data (DMSO-d6): 6.61-6.87 (m, 1H, NH); 4.85 (br.s, 1H, OH); 3.77-3.92 (m, 1H); 2.90 (t, 2H, CH2, J=6.1 Hz); 2.10-2.22 (m, 2H); 1.67-1.80 (m, 1H); 1.21-1.51 (m, 11H, CH2, Boc).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. customevaporated
  3. customThe residue was recrystallized form ether

Sources & evidence

ORD record
ord-4637e6dbb2844822aebf761cd1d20019
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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