Lawesson's reagent → HCID 54313871, compound

HRID 849877Notes

Reaction equation

HRID 849877 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)[C:10]([NH2:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:33]2)=CC=1>O1CCOCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:10](=[S:33])[NH2:12])[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 54289233HCID 54289233, compound

Product 1

HCID 54313871HCID 54313871, compoundYield 157.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionic acid amide (1.058 g; 3.36 mmol) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) (0.71 g; 1.76 mmol) were dissolved in dioxane (6 ml). The reaction mixture was heated 30 min at 60° C. and stirred 12 hours at room temperature. The solvent was removed in vacuo and to the residue was added a mixture of water/sodium hydrogencarbonate (1:1; 15 ml) and stirred 30 min at room temperature. The mixture was filtered. The solid was washed with water (2×5 ml) and chromatographed on silica (2×15 cm) using ethyl acetate/heptane (2:1) to afford 0.914 g of ((1R)-2-(2-naphthyl)-1-thiocarbamoylethyl)carbamic acid tert-butylester.

Workup

  1. customThe solvent was removed in vacuo and to the residue
  2. additionwas added
  3. additiona mixture of water/sodium hydrogencarbonate (1:1; 15 ml)
  4. stirringstirred 30 min at room temperature
  5. filtrationThe mixture was filtered
  6. washThe solid was washed with water (2×5 ml)
  7. customchromatographed on silica (2×15 cm)

Sources & evidence

ORD record
ord-bd2f0720c46944269e923f703f348e34
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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