Carbon Disulfide → 3-(4,4'-Dimethoxytrityloxymethyl)benzyl isothiocyanate

HRID 473228Notes

Reaction equation

HRID 473228 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[CH2:27][NH2:28])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C:34](=S)=[S:35].C(N(CC)CC)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CCO.CN(C1C=CN=CC=1)C>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[CH2:27][N:28]=[C:34]=[S:35])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:33][CH:32]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 672534783-(4,4'-Dimethoxytrityloxymethyl)benzylamine

Product 1

HCID 866715143-(4,4'-Dimethoxytrityloxymethyl)benzyl isothiocyanate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent3×

Procedure

3-(4,4′-Dimethoxytrityloxymethyl)benzylamine (5) (613 mg, 1.39 mmol), carbon disulfide (0.85 mL, 13.9 mmol, 10 eq.), and triethylamine (0.20 mL, 1.39 mmol) were dissolved in EtOH (2 mL). The air was evacuated from the reaction system, and then Ar was charged therein. The reaction mixture was stirred for 2 hours at a room temperature. Then, in an ice bath, to the mixture were added dropwise a solution of di-tert-butyl dicarbonate (3.06 mg, 1.40 mmol) in EtOH (0.6 mL) and a solution of DMAP (6.12 mg, 6 mol %) in EtOH (0.6 mL). The mixture was further stirred for 4 hours at a room temperature. TLC was used to confirm there was no starting material in the mixture. Then, the reaction mixture was evaporated under reduced pressure. The residue was purified by column chromatography (Hex:EtOAc=10:1) to isolate

Workup

  1. customThe air was evacuated from the reaction system
  2. additionAr was charged
  3. stirringThe mixture was further stirred for 4 hours at a room temperature
  4. customThen, the reaction mixture was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (Hex:EtOAc=10:1)
  6. customto isolate

Sources & evidence

ORD record
ord-7d780b52f8d847259b6fa272c4609f83
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

Loading…