Carbamic acid, (isocyanatomethyl)-, 9H-fluoren-9-ylmethyl ester → HCID 44128898, compound

HRID 2098309Notes

Reaction equation

HRID 2098309 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:22])[NH:17][CH2:18][N:19]=[C:20]=[O:21])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:23](=[C:25]1[N:29]=[CH:28][N:27]=[C:26]1[C:30]([NH2:32])=[O:31])=[N-:24]>CS(C)=O>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:22])[NH:17][CH2:18][N:19]3[C:20](=[O:21])[N:29]4[CH:28]=[N:27][C:26]([C:30](=[O:31])[NH2:32])=[C:25]4[N:23]=[N:24]3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11483252Carbamic acid, (isocyanatomethyl)-, 9H-fluoren-9-ylmethyl esterHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 44128898HCID 44128898, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Isocyanatomethyl-carbamic acid 9H-fluoren-9-ylmethyl ester (1.13 g, 3.83 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.5 g, 3.65 mmol) in dry dimethylsulfoxide (5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the pouring onto crushed ice. The resultant precipitate was collected by filtration and washed with Et2O (3 reaction volumes) and dried to give the title compound as a white solid (600 mg, 33.9%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.86 (1H, s), 8.61 (1H, t-broad), 7.89-7.26 (9H, m), 5.55 (2H, t, J=6.8 Hz), 4.40-4.19 (5H, m), 2.01 (2H, s).

Workup

  1. customThe reaction was quenched by the pouring
  2. customonto crushed ice
  3. filtrationThe resultant precipitate was collected by filtration
  4. washwashed with Et2O (3 reaction volumes)
  5. customdried

Sources & evidence

ORD record
ord-f4ce4d99ea434a85a641da6e1fc25af4
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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