Triethylamine → HCID 9920758, compound

HRID 983684Notes

Reaction equation

HRID 983684 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[CH3:25][O:26][C:27]([CH2:29][C@@:30]1([CH2:36]C(O)=O)[CH2:34][CH2:33][C@@H:32]([CH3:35])[CH2:31]1)=[O:28]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:25][O:26][C:27](=[O:28])[CH2:29][C@@:30]1([CH2:36][N:20]=[C:23]=[O:8])[CH2:34][CH2:33][C@@H:32]([CH3:35])[CH2:31]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58626982HCID 58626982, compound

Product 1

HCID 9920758HCID 9920758, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diphenylphosphoryl azide (8.07 mL, 37.4 mmol), triethylamine (5.36 mL, 39 mmol), and ((1S,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl)-acetic acid (7.93 g, 37 mmol) were refluxed in toluene (80 mL) for 17 hours. The mixture was allowed to cool and then taken up in ethyl acetate (250 mL), washed with saturated aqueous sodium hydrogen carbonate (250 mL), brine (100 mL), and dried (MgSO4). The solvent was removed under reduced pressure to give 7.82 g (100%) of ((1R,3R)-1-isocyanatomethyl-3-methyl-cyclopentyl)-acetic acid methyl ester which was used without further purification;

Workup

  1. temperatureto cool
  2. washwashed with saturated aqueous sodium hydrogen carbonate (250 mL), brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-30252652f10f4b46891ba4d068f5c1b9
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

Loading…