Ethyl isothiocyanate → HCID 42600800, compound

HRID 875272Notes

Reaction equation

HRID 875272 reaction equation
Cl.[OH:2][C:3]12[CH2:36][CH2:35][C@@:34]3([CH3:37])[C:29](=[C:30]([CH3:38])[CH2:31][CH2:32][CH2:33]3)[C@H:4]1[O:5][C:6](=[O:28])[CH:7]2[CH2:8][NH:9][CH2:10][CH:11]1[C:15](=[O:16])[O:14][C@H:13]2[C:17]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C:12]12[OH:27])[CH2:21][CH2:20][CH2:19][C:18]=3[CH3:26].[CH2:39]([N:41]=[C:42]=[S:43])[CH3:40]>O1CCCC1>[CH2:39]([NH:41][C:42](=[S:43])[N:9]([CH2:10][CH:11]1[C:15](=[O:16])[O:14][C@H:13]2[C:17]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C:12]12[OH:27])[CH2:21][CH2:20][CH2:19][C:18]=3[CH3:26])[CH2:8][CH:7]1[C:6](=[O:28])[O:5][C@@H:4]2[C:29]3[C@:34]([CH3:37])([CH2:35][CH2:36][C:3]12[OH:2])[CH2:33][CH2:32][CH2:31][C:30]=3[CH3:38])[CH3:40]

Participants

4

Reactant 2

HCID 10966Ethyl isothiocyanateHCID 66842649HCID 66842649, compound

Product 1

HCID 42600800HCID 42600800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

The compound obtained in step 1 of example 55 (200 mg, 0.389 mmole) was dissolved in dry tetrahydrofuran (10 mL) and to it ethyl isothiocyanate (54.22 mg, 0.62 mmole) was added dropwise. The reaction mixture was stirred at room temperature (25° C.) for 3 hours. Reaction mixture was concentrated and crude product was purified by column chromatography (silica gel, 20% ethyl acetate in petroleum ether) to obtain the title compound.

Workup

  1. additionwas added dropwise
  2. customReaction mixture
  3. concentrationwas concentrated
  4. customcrude product was purified by column chromatography (silica gel, 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d08e1ee1392b4dcb9ad6af94dc1d9ffc
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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