Methanol → HCID 86760802, compound

HRID 2378114Notes

Reaction equation

HRID 2378114 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH:36]([O:39][C:40]([N:42]1[C:51]2[C:46](=[N:47][C:48]([O:52][CH3:53])=[CH:49][CH:50]=2)[C@H:45]([N:54]([CH2:60][C:61]2[CH:66]=[C:65]([C:67]([F:70])([F:69])[F:68])[CH:64]=[C:63]([C:71]([F:74])([F:73])[F:72])[CH:62]=2)[C:55]2[N:56]=[N:57][NH:58][N:59]=2)[CH2:44][C@@H:43]1[CH2:75][CH3:76])=[O:41])([CH3:38])[CH3:37]>ClCCl>[CH:36]([O:39][C:40]([N:42]1[C:51]2[C:46](=[N:47][C:48]([O:52][CH3:53])=[CH:49][CH:50]=2)[C@H:45]([N:54]([CH2:60][C:61]2[CH:66]=[C:65]([C:67]([F:68])([F:69])[F:70])[CH:64]=[C:63]([C:71]([F:72])([F:73])[F:74])[CH:62]=2)[C:55]2[N:56]=[N:57][N:58]([CH3:1])[N:59]=2)[CH2:44][C@@H:43]1[CH2:75][CH3:76])=[O:41])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86760800HCID 86760800, compound

Product 1

HCID 86760802HCID 86760802, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add triphenylphosphine (27 mg, 0.104 mmol), methanol (17 mg, 0.52 mmol), and diisopropylazodicarboxylate (0.018 mL, 0.104 mmol) to a solution of (+/−)-cis-4-[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester in dry dichloromethane (1 mL) and stir the mixture for 15 h at room temperature. Remove the solvent in vacuo and purify the residue by silica gel chromatography, eluting with ethyl acetate/hexanes to afford the title compound (41 mg, 66%). MS (ES+): 602 (M+H).

Workup

  1. customRemove the solvent in vacuo
  2. custompurify the residue by silica gel chromatography
  3. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-af48823d16194497a7df7f730a491875
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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