HCID 90253557, compound → HCID 90253540, compound

HRID 1478775Notes

Reaction equation

HRID 1478775 reaction equation
[OH:1][N:2]=[CH:3][CH2:4][O:5][C@@H:6]([C@@H:10]1[CH2:14][CH2:13][CH2:12][O:11]1)[CH2:7][CH:8]=[CH2:9].C[C@@H]1C[C@H]1C1OCC2=NOCC2C1>>[O:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C@@H:6]1[O:5][CH2:4][C:3]2=[N:2][O:1][CH2:9][C@@H:8]2[CH2:7]1

Participants

3

Reactant 2

HCID 90253557HCID 90253557, compoundHCID 118621156HCID 118621156, compound

Product 1

HCID 90253540HCID 90253540, compound

Procedure

N-Hydroxy-2-({(1R)-1-[(2S)-tetrahydrofuran-2-yl]but-3-en-1-yl}oxy)ethanimine (C98) was converted to the product using the method described for the synthesis of 5-[(1R,2R)-2-methylcyclopropyl]-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazole (C85) in Example 20. Yield: 2.6 g, 13 mmol, 54%. LCMS m/z 198.0 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 4.73 (d, J=13.1 Hz, 1H), 4.61 (dd, J=10.0, 8.0 Hz, 1H), 4.19 (dd, J=13.6, 1 Hz, 1H), 3.72-3.89 (m, 4H), 3.38-3.48 (m, 2H), 2.35 (ddd, J=12.9, 6.4, 1.3 Hz, 1H), 1.78-2.02 (m, 4H), 1.44-1.53 (m, 1H).

Sources & evidence

ORD record
ord-54792a29767141b0b988b137e184adec
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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