Diisopropylethylamine → HCID 71245383, compound

HRID 1186016Notes

Reaction equation

HRID 1186016 reaction equation
[CH2:1]([C:8]1([C:23]([OH:25])=O)[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O:27][C:28](=[O:34])[C@H:29]([C@@H:31]([CH3:33])[OH:32])[NH2:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH2:16]([O:15][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C:8]1([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:23](=[O:25])[NH:30][C@@H:29]([C@H:31]([OH:32])[CH3:33])[C:28]([O:27][CH3:26])=[O:34])=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2734894L-Threonine methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15282610HCID 15282610, compound

Product 1

HCID 71245383HCID 71245383, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of compound 3 (1.0 g, 2.94 mmol), L-threonine methyl ester (471 mg, 3.53 mmol) in DMF (20 mL) was added HATU (1.12 g, 2.94 mmol) and DIPEA (1.58 mL, 8.84 mmol) at 5° C. The reaction mixture was stirred at RT for 16 h. It was diluted with EtOAc (150 mL) and washed with water (2×30 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography 50% EtOAc/Hexane as eluent to yield compound 4 (1.0 g, 74%).

Workup

  1. washwashed with water (2×30 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography 50% EtOAc/Hexane as eluent

Sources & evidence

ORD record
ord-4fb2abf2e9144a2dafe2a8cab802dadf
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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