Dimethylformamide → Fmoc-Pro-Pro-OH

HRID 1927793Notes

Reaction equation

HRID 1927793 reaction equation
[N:1]1([C:9](OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C1CN([P+](ON2N=N[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:59]([N:62]([CH:65]([CH3:67])C)[CH2:63][CH3:64])(C)C.N1[C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[C:71](=O)[C:69]1=[O:70].CN(C=[O:83])C>C(Cl)Cl>[N:62]1([C:59]([O:70][CH2:69][CH:71]2[C:45]3[C:44](=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:78]3[C:73]2=[CH:74][CH:75]=[CH:76][CH:77]=3)=[O:83])[CH2:63][CH2:64][CH2:67][C@H:65]1[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:10]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 7054IsatinHCID 81531DiisopropylethylamineHCID 688135Fmoc-Pro-OH2×HCID 2724699PyBOP

Product 1

HCID 11133845Fmoc-Pro-Pro-OH

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Resin from step A was swollen with CH2Cl2 (1×10 min) then further washed with DMF three times. The Fmoc group was removed with 20% piperidine in DMF for 30 min. Further resin washings were done with DMF (3×2 min), CH2Cl2 (3×2 min) and DMF (1×1 min). Then Fmoc-L-Proline (1.5 mmol, 2.5 equivalents with respect to initial resin loading), PyBop® (1.5 mmol) and diisopropylethylamine (3 mmol) together in DMF (10 ml) were added to the resin. The resin was shaken at room temperature for 60 min. A small sample of resin was submitted for isatin test for completion of reaction. The resin was filtered and washed with DMF (3×2 min), CH2Cl2 (2×2 min), MeOH (2×2 min), CH2Cl2 (2×2 min) and MeOH (3×2 min).

Workup

  1. washthen further washed with DMF three times
  2. customThe Fmoc group was removed with 20% piperidine in DMF for 30 min
  3. customwere done with DMF (3×2 min), CH2Cl2 (3×2 min) and DMF (1×1 min)
  4. filtrationThe resin was filtered
  5. washwashed with DMF (3×2 min), CH2Cl2 (2×2 min), MeOH (2×2 min), CH2Cl2 (2×2 min) and MeOH (3×2 min)

Sources & evidence

ORD record
ord-0bb71be4e7b04344846772e9bf8bd734
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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