Diisopropylethylamine → HCID 11134039, compound

HRID 2306173Notes

Reaction equation

HRID 2306173 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[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.[CH2:50]([O:57][C:58]1[CH:59]=[C:60]([CH:63]=[CH:64][CH:65]=1)[CH2:61][NH2:62])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[C:14]([NH:62][CH2:61][C:60]1[CH:63]=[CH:64][CH:65]=[C:58]([O:57][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:59]=1)=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111051N-(tert-Butyloxycarbonyl)-D-methionineHCID 2724699PyBOPHCID 11009288(3-(Benzyloxy)phenyl)methanamine

Product 1

HCID 11134039HCID 11134039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (R)-N-(tert-butoxycarbonyl)methionine (1.20 g, 4.8 mmol) in dry CH2Cl2 (25 mL) under argon were added PYBOP (2.90 g, 5.6 mmol), 3-benzyloxybenzylamine, as described above in Step I, (1.0 g, 4.7 mmol), and N,N-diisopropylethylamine (0.89 mL, 5.1 mmol). The reaction mixture was stirred for 18 hours, then extracted with saturated aqueous NaHCO3 (25 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—25% EtOAc to yield the product as a white solid.

Workup

  1. extractionextracted with saturated aqueous NaHCO3 (25 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography on silica
  6. washeluting with hexane—25% EtOAc

Sources & evidence

ORD record
ord-33b5bc28b7744f08ae73ace5161c1417
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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