Triethylamine → HCID 58626984, compound

HRID 983690Notes

Reaction equation

HRID 983690 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 58626993HCID 58626993, compound

Product 1

HCID 58626984HCID 58626984, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diphenylphosphoryl azide (5.35 mL, 24.8 mmol), triethylamine (3.55 mL, 25.6 mmol), and [(1R,3R)-1-methoxycarbonylmethyl-3-methyl-cyclopentyl]-acetic acid (5.26 g, 24.5 mmol) were refluxed in toluene (80 mL) for 17 hours. The mixture was allowed to cool and then taken up in ethyl acetate (300 mL), washed with saturated aqueous sodium hydrogen carbonate solution (250 mL), brine (200 mL), and dried (MgSO4). The solvent was removed under reduced pressure to give 5.19 g (100%) of ((1S,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 solution (250 mL), brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eae35b823caf4a1f9ca690f4cb388aa2
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

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