Triethylamine → HCID 178454300, compound

HRID 1441363Notes

Reaction equation

HRID 1441363 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7]/[C:8](=[N:16]/[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])/S(C(F)(F)F)(=O)=O)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:42][CH:41]([OH:43])[CH2:40]2)=[CH:35][CH:34]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[NH:7]/[C:8](/[NH:32][C:33]1[CH:34]=[CH:35][C:36]([N:39]2[CH2:40][CH:41]([OH:43])[CH2:42]2)=[CH:37][CH:38]=1)=[N:16]/[C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 45088832HCID 45088832, compoundHCID 87540273tert-butyl (NZ)-N-[[(2-methylpropan-2-yl)oxycarbonylamino]-(trifluoromethylsulfonyl)methylidene]carbamate

Product 1

HCID 178454300HCID 178454300, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {[(Z)-tert-butoxycarbonylimino]-trifluoromethanesulfonyl-methyl}-carbamic acid tert-butyl ester (13.62 g, 34.8 mM) and triethylamine (4.9 ml, 34.8 mM) in dry DCM (183 ml), 1-(4-aminophenyl)azetidin-3-ol (Method 37; 6.0 g, 36.5 mM) was added. The solution was stirred at room temperature under nitrogen for 48 hours. The reaction mixture was diluted with more DCM and washed with water (twice), saturated sodium bicarbonate solution (twice), water and saturated sodium chloride. The solution was then dried with anhydrous sodium sulphate, filtered and evaporated. The crude product was triturated with ether/isohexane (2:1), filtered washed with the same solvent and dried to give the title compound as a yellow solid (11.77 g, 83%). NMR 1.4 (s, 9H), 1.5 (s, 9H), 3.47 (t, 1H), 4.02 (t, 2H), 4.5 (m, 1H), 5.55 (d, 1H), 6.38 (d, 2H), 7.23 (d, 2H), 9.75 (s, 1H), 11.46 (m, 1H); m/z 407.

Workup

  1. washwashed with water (twice), saturated sodium bicarbonate solution (twice), water and saturated sodium chloride
  2. dry with materialThe solution was then dried with anhydrous sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was triturated with ether/isohexane (2:1)
  6. filtrationfiltered
  7. washwashed with the same solvent
  8. customdried

Sources & evidence

ORD record
ord-c48bc523271e470f9baf2d552585fea4
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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