Benzyl Alcohol → HCID 23589540, compound

HRID 1609897Notes

Reaction equation

[CH2:1]([C:3]1[C:4](C(O)=O)=[CH:5][N:6]2[C:11]=1[C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)=[N:9][CH:8]=[N:7]2)[CH3:2].C([N:26]([CH2:29]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1.[CH2:48]([OH:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>O1CCOCC1>[C:49]1([CH2:48][O:55][C:29](=[O:38])[NH:26][C:4]2[C:3]([CH2:1][CH3:2])=[C:11]3[N:6]([CH:5]=2)[N:7]=[CH:8][N:9]=[C:10]3[NH:12][C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of Example 84 (36 mg, 0.12 mmol) in 1,4-dioxane (1.4 mL) under argon with powdered 4 Å molecular sieves was added triethylamine (19 μL, 0.14 mmol, 1.2 eq) and diphenylphosphoryl azide (30 μL, 0.14 mmol). The mixture was heated at 85° C. for 1 hr and then benzyl alcohol (24 μL, 0.23 mmol) was added. The reaction mixture was warmed at 85° C. for 15 hrs. The mixture was filtered, concentrated in vacuo, and purified directly by rotary chromatography directly on a 1 mm silica gel plate eluting with 2% methanol in chloroform to provide 29 mg (60%) of yellow oil. MS: [M+H]+=419.2; 1H NMR (CDCl3): δ 8.27 (d, J=2.7 Hz, 1H), 7.98 (s, 1H), 7.95 (dd, J=8.8, 2.7 Hz, 1H), 7.90 (s, 1H), 7.43-7.35 (m, 5H), 6.81 (d, J=8.8 Hz, 1H), 6.46 (br s, 1H), 5.24 (s, 2H), 3.96 (s, 3H), 2.82 (q, J=7.7 Hz, 2H), 1.34 (t, J=7.7 Hz, 3H).

Workup

temperatureThe reaction mixture was warmed at 85° C. for 15 hrs
filtrationThe mixture was filtered
concentrationconcentrated in vacuo
custompurified directly by rotary chromatography directly on a 1 mm silica gel plate
washeluting with 2% methanol in chloroform

Sources & evidence

ORD record: ord-e5c4a97b4d58443887a2d2a9869a7a76
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982265B1

Reaction notes

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