Dimethylformamide → HCID 67061815, compound

HRID 2167009Notes

Reaction equation

HRID 2167009 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]([C:32]([OH:34])=[O:33])[NH:14]C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:46][O:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52]Cl)=[CH:50][CH:49]=1>CCCCCC.CCOC(C)=O>[CH3:46][O:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52][O:34][C:32](=[O:33])[CH:13]([NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 2724628Fmoc-Lys(Boc)-OH

Product 1

HCID 67061815HCID 67061815, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Compound 2 was prepared in two steps. Into a 250 mL, flame dried three necked round bottom flask under nitrogen was placed Nε-Boc-Nα-Fmoc-L-lysine (7.0 g, 15 mmol) and 60 mL of dry DMF. To this was added cesium carbonate (7 g, 21 mmol) and 4-methoxybenzyl chloride (2.5 g, 16 mmol). The suspension was stirred at room temperature under nitrogen for 4 h, then filtered and washed with ethyl acetate. Product isolation (EtOAc, 5% Na2CO3, water, Na2SO4) followed by recrystallization from 60/40 (v/v) hexane/EtOAc gave 2 crops of a colorless solid. mp 118-120° C. TLC Rf=0.33 (70/30 Hexane/EtOAc). Yield: 8.22 g, 14 mmol, 93.43%. 1H NMR(CDCl3) δ: 7.75 (d, J=7.2 Hz, 2H), 7.55 (d, J=7.2 Hz, 2H), 7.38 (t, J=7.5 Hz, 2H), 7.32-7.20 (m, 4H), 6.85-6.80 (m, 2H), 5.4 (d, J=7.6 Hz, 1H), 5.18-5.00 (m, 2H), 4.44-4.38 (m, 3H), 4.17 (t, J=6.0 Hz 1H), 3.80-3.70 (m, 4H), 3.00 (m, 2H), 1.90-1.11 (m, 15H). ESIMS m/z: 588.40 [M+1]+.

Workup

  1. temperatureInto a 250 mL, flame
  2. customdried three necked round bottom flask under nitrogen
  3. filtrationfiltered
  4. washwashed with ethyl acetate
  5. customProduct isolation (EtOAc, 5% Na2CO3, water, Na2SO4) followed by recrystallization from 60/40 (v/v) hexane/EtOAc
  6. customgave 2 crops of a colorless solid

Sources & evidence

ORD record
ord-e11f7fd7c7f24010a07b581eec5034cc
Source dataset
uspto-grants-2015_06
Patent number
US09044468B2

Reaction notes

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