Lawesson's reagent → HCID 86751653, compound

HRID 2294718Notes

Reaction equation

HRID 2294718 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[S:41])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86751652HCID 86751652, compound

Product 1

HCID 86751653HCID 86751653, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 14.8 g (33.9 mmol) of 4-benzyl 1-tert-butyl N-[(1-tert-butoxyformamido)acetyl]-L-aspartate and 6.9 g (17 mmol) of Lawesson reagent in 140 ml of dry toluene is heated to 100° for 2.5 hours. Thereafter, the solvent is distilled off under reduced pressure and the residue is boiled up three times with 500 ml of a 9:1 mixture of hexane and ether. The combined organic phases are evaporated and, for purification, the residue is chromatographed on silica gel using a 9:1 mixture of hexane and ether as the eluent, whereby there is obtained 4-benzyl 1-tert-butyl N-[(1-tert-butoxyformamido)thioacetyl]-L-aspartate as a viscous oil; MS: 452 (M)+.

Workup

  1. distillationThereafter, the solvent is distilled off under reduced pressure
  2. additionwith 500 ml of a 9:1 mixture of hexane and ether
  3. customThe combined organic phases are evaporated and, for purification
  4. customthe residue is chromatographed on silica gel using
  5. additiona 9:1 mixture of hexane and ether as the eluent

Sources & evidence

ORD record
ord-5167ec7e38564f6cb19af157c225b03d
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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