Triethylamine → tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

HRID 1766826Notes

Reaction equation

HRID 1766826 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(N(CC)CC)C.[C:20]([O:24][C:25]([NH:27][CH2:28][CH2:29]OS(C)(=O)=O)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.C(OCC)(=O)C>[C:20]([O:24][C:25](=[O:26])[NH:27][CH2:28][CH2:29][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Product 1

HCID 18929164tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Added N-hydroxyphthalimide (1.12 g, 6.87 mmol) and triethylamine (0.96 mL, 6.87 mmol) to a solution of methanesulfonic acid 2-tert-butoxycarbonylamino-ethyl ester (1.37 g, 5.73 mmol) in DMF (20 mL). The solution was heated to 50° C. for 16 hours after which time it was cooled to room temperature. The solution was diluted with ethyl acetate, washed with water (2×), saturated K2CO3, dried over Na2SO4 and concentrated to an orange solid (747 mg, 43%) which was taken on without purification.

Workup

  1. temperaturewas cooled to room temperature
  2. washwashed with water (2×), saturated K2CO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to an orange solid (747 mg, 43%) which
  5. customwas taken on without purification

Sources & evidence

ORD record
ord-e4d7d25ddca54939bc63e9a9559624e7
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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