Isothiocyanatotrimethylsilane → 5-(1H-Indol-3-ylmethyl)-2-thioxo-4-imidazolidinone

HRID 401606Notes

Reaction equation

HRID 401606 reaction equation
Cl.CO[C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].C(N(C(C)C)CC)(C)C.C[Si]([N:31]=[C:32]=[S:33])(C)C>ClCCl.CN(C1C=CN=CC=1)C.CC(O)=O.CCOC(C)=O>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH2:7][CH:5]2[NH:6][C:32](=[S:33])[NH:31][C:4]2=[O:17])=[CH:9]1

Participants

8

Reactant 3

HCID 75297IsothiocyanatotrimethylsilaneHCID 81531DiisopropylethylamineHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 53717615-(1H-Indol-3-ylmethyl)-2-thioxo-4-imidazolidinoneYield 94%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of L-tryptophan methyl ester hydrochloride (0.257 mg, 0.001 mol.) in dichloromethane (10 mL) was added DMAP (5.0 mg), diisopropylethylamine (10 eq.) and then trimethylsilylisothiocyanate (1.3 gm, 0.01 mol.). The reaction mixture was stirred at room temperature for 24 hr, and then concentrated. The residue obtained was dissolved in AcOH (10 mL) and refluxed for 6 h. The reaction mixture was concentrated and dried under vacuum. The solid obtained was suspended in EtOAc, filtered, washed with EtOAc, and dried under vacuum to give 893-18 (230 mg, 94%): mp 206-210° C., 1H NMR (500 MHz, DMSO-d6): 3.00—yield 34%, 1H NMR (500 MHz, CDCl3): 3.24-3.33 (m, 2H), 4.23-4.26 (m, 1H), 7.01 (dd, J=8.0 and 7.0 Hz, 1H), 7.09 (dd, J=8.0 and 7.0 Hz, 1H), 7.23 (d, J=2.0 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 1H), 8.50 (s, 2H), 11.08 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. temperaturerefluxed for 6 h
  4. concentrationThe reaction mixture was concentrated
  5. customdried under vacuum
  6. customThe solid obtained
  7. filtrationfiltered
  8. washwashed with EtOAc
  9. customdried under vacuum

Sources & evidence

ORD record
ord-80e394ff567d4fb39fdd86cc698dd1a5
Source dataset
uspto-grants-2014_06
Patent number
US08741942B2

Reaction notes

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