Diisopropylethylamine → HCID 18475855, compound

HRID 2187892Notes

Reaction equation

HRID 2187892 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:45]([Si:48]([CH:66]([CH3:68])[CH3:67])([CH:63]([CH3:65])[CH3:64])[O:49][C:50]1[CH:59]=[C:58]2[C:53]([CH:54]=[CH:55][CH:56]=[C:57]2[C:60](O)=[O:61])=[CH:52][CH:51]=1)([CH3:47])[CH3:46].C(N(CC)C(C)C)(C)C>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:60]([C:57]1[C:58]2[C:53](=[CH:52][CH:51]=[C:50]([O:49][Si:48]([CH:63]([CH3:65])[CH3:64])([CH:66]([CH3:68])[CH3:67])[CH:45]([CH3:46])[CH3:47])[CH:59]=2)[CH:54]=[CH:55][CH:56]=1)=[O:61])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 2724699PyBOPHCID 18536004HCID 18536004, compound

Product 1

HCID 18475855HCID 18475855, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(tert-butoxycarbonylamino)ethylamine (70 mg, 0.44 mmol) in dry THF (1 mL) under argon were added PYBOP (226 g, 0.43 mmol), 7-(triisopropylsilyloxy)-1-naphthoic acid, as described above in Step D, (148 mg, 0.43 mmol), and N,N-diisopropylethylamine (0.115 mL, 0.66 mmol). The reaction mixture was stirred for 4 hrs, then partitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (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 a gradient of CH2Cl2 −10% to 15% EtOAc to yield the desired product as a white solid.

Workup

  1. custompartitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (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 a gradient of CH2Cl2 −10% to 15% EtOAc

Sources & evidence

ORD record
ord-1e740f4e61bd4d2d9bc617ac9d30799e
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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