Diisopropylethylamine → HCID 69785992, compound

HRID 2187888Notes

Reaction equation

HRID 2187888 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])=[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.[CH3:47][O:48][CH2:49][CH2:50][O:51][CH2:52][O:53][C:54]1[CH:63]=[C:62]2[C:57]([CH:58]=[CH:59][CH:60]=[C:61]2[NH:64][CH3:65])=[CH:56][CH:55]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:10])[C:11]([N:64]([C:61]1[C:62]2[C:57](=[CH:56][CH:55]=[C:54]([O:53][CH2:52][O:51][CH2:50][CH2:49][O:48][CH3:47])[CH:63]=2)[CH:58]=[CH:59][CH:60]=1)[CH3:65])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 2724699PyBOPHCID 18475823HCID 18475823, compound

Product 1

HCID 69785992HCID 69785992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (R)-N-(tert-butoxycarbonyl)alanine (1.09 g, 5.78 mmol) in dry CH2Cl2 (4 mL) under argon were added PYBOP (3.01 g, 5.78 mmol), 7-[(2-methoxyethoxy)methoxy]-1-(methylamino)naphthalene, as described above in Step B, (302 mg, 1.16 mmol), and N,N-diisopropylethylamine (1.00 mL, 5.75 mmol). The reaction mixture was stirred for 48 hrs, then partitioned between CH2Cl2 (500 mL) and 10% aqueous citric acid (150 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 hexane −10% to 60% EtOAc to yield the desired product.

Workup

  1. custompartitioned between CH2Cl2 (500 mL) and 10% aqueous citric acid (150 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 hexane −10% to 60% EtOAc

Sources & evidence

ORD record
ord-91222a94e94a4889bf5fc81647edb445
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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