Triethylamine → 9-Fluorenylmethyl carbamate

HRID 2167056Notes

Reaction equation

HRID 2167056 reaction equation
[C:1](C(N)CN)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].C([N:24](CC)CC)C>CN(C=O)C>[C:1]([NH2:24])([O:3][CH2:4][CH:5]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 21106254HCID 21106254, compound

Product 1

HCID 7363019-Fluorenylmethyl carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of Fmoc-1,2-diaminoethane (0.06 mmol) in 0.4 mL DMF at 0° C., is added triethylamine (0.12 mmol) followed by dropwise addition of DOTA(OtBu)3 NHS ester (0.05 mmol) in 0.5 mL DMF for 10 min with stirring. After 10 min, the ice bath is removed and stirring is continued at room temperature (RT) for 6 h. The reaction mixture is poured over 2 mL ice-cold water and purified by preparative HPLC. After concentration and lyophilization, Fmoc amine monomer 23 is obtained which is further treated with 1 mL 20% piperidine in DMF, and the solution is stirred at RT for 30 min. The reaction mixture is poured over 2 mL ice-cold water and purified by preparative HPLC. After lyophilization, DOTA(OtBu)3-aminoethane 24 is obtained.

Workup

  1. customthe ice bath is removed
  2. stirringstirring
  3. customis continued at room temperature
  4. custom(RT)
  5. customfor 6 h
  6. additionThe reaction mixture is poured over 2 mL ice-cold water
  7. custompurified by preparative HPLC
  8. concentrationAfter concentration and lyophilization

Sources & evidence

ORD record
ord-cc25dfd31c0d451f868844282b4dd6ad
Source dataset
uspto-grants-2015_06
Patent number
US09044505B2

Reaction notes

Loading…