Diisopropylethylamine → HCID 18475827, compound

HRID 2187894Notes

Reaction equation

HRID 2187894 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:41]([Si:44]([CH:62]([CH3:64])[CH3:63])([CH:59]([CH3:61])[CH3:60])[O:45][C:46]1[CH:55]=[C:54]2[C:49]([CH:50]=[CH:51][CH:52]=[C:53]2[C:56](O)=[O:57])=[CH:48][CH:47]=1)([CH3:43])[CH3:42].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:56]([C:53]1[C:54]2[C:49](=[CH:48][CH:47]=[C:46]([O:45][Si:44]([CH:59]([CH3:61])[CH3:60])([CH:62]([CH3:64])[CH3:63])[CH:41]([CH3:42])[CH3:43])[CH:55]=2)[CH:50]=[CH:51][CH:52]=1)=[O:57]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 2724699PyBOPHCID 18536004HCID 18536004, compound

Product 1

HCID 18475827HCID 18475827, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To glycine methyl ester hydrochloride (140 mg, 1.12 mmol) in dry DMF (1 mL) under argon were added PYBOP (233 g, 0.45 mmol), 7-(triisopropylsilyloxy)-1-naphthoic acid, as described in Example 30, Step D, (155 mg, 0.45 mmol), and N,N-diisopropylethylamine (0.31 mL, 1.78 mmol). The reaction mixture was stiffed for 3 hrs, then partitioned between CH2Cl2 (50 mL) and H2O (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with CH2Cl2-5% EtOAc to yield the desired product as a colorless oil.

Workup

  1. custompartitioned between CH2Cl2 (50 mL) and H2O (20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with CH2Cl2-5% EtOAc

Sources & evidence

ORD record
ord-7ae6fa2b39724c96b86f37150fa6af6b
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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