Lawesson's reagent → HCID 88191236, compound

HRID 2306203Notes

Reaction equation

HRID 2306203 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:10]1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:10]1=[S:42])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 70171512HCID 70171512, compound

Product 1

HCID 88191236HCID 88191236, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (R)-3-(tert-butoxycarbonylamino)-1-[7-(tert-butyl-dimethylsilyloxy)naphthalen-1-yl]-2-oxopyrrolidine, as described above in Step F, (113 mg, 0.247 mmol) and Lawesson's Reagent (50 mg, 0.124 mmol) in dry toluene (0.5 mL), under argon, was heated to 80° C. for 1 hour. The reaction mixture was allowed to cool, then poured directly onto a silica gel column and chromatographed, eluting with a gradient of hexane—5% to 25% EtOAc to yield the titled product as a clear oil.

Workup

  1. temperatureto cool
  2. additionpoured directly onto a silica gel column
  3. customchromatographed
  4. washeluting with a gradient of hexane—5% to 25% EtOAc

Sources & evidence

ORD record
ord-7674f4687adb431eb93a72ef2b0eaedc
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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