Dimethylformamide → HCID 131727160, compound

HRID 269654Notes

Reaction equation

HRID 269654 reaction equation
CN(C([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:28]([CH2:32]C)C(C)C)(C)C.[C:34]([O:38][C:39]([NH:41][C@H:42]([C:45]([OH:47])=O)[CH2:43][OH:44])=[O:40])([CH3:37])([CH3:36])[CH3:35].Cl.[CH2:49](N(CCN)C(=O)O)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C[N:64]([CH:66]=[O:67])[CH3:65]>>[CH2:49]([O:8][C:66](=[O:67])[NH:64][CH2:65][CH2:32][NH:28][C:45](=[O:47])[C@H:42]([CH2:43][OH:44])[NH:41][C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:40])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19805659HCID 19805659, compound

Product 1

HCID 131727160HCID 131727160, compound

Procedure

627.4 mg (1.650 mmol) of HATU and 387.7 mg (3.0 mmol) of N,N-diisopropylethylamine are added to a solution of 307.8 mg (1.50 mmol) of N-(tert-butoxycarbonyl)-L-serine in 25 ml of anhydrous DMF. After stirring at RT for 15 min, 380.6 mg (1.650 mmol) of benzyl(2-aminoethyl)carbamate hydrochloride are added. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is taken up in dichloromethane. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The crude product is purified by preparative HPLC.

Workup

  1. stirringThe reaction mixture is stirred at RT for 15 h
  2. customThe solvent is then evaporated
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-80dfc607f0714e7eaf7782780a9028a4
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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