HCID 58764221, compound → HCID 58764145, compound

HRID 2387053Notes

Reaction equation

[CH:1]1([C:6]([OH:30])([C:17]#[C:18][C:19]2[CH:24]=[C:23]([F:25])[C:22]([CH2:26][OH:27])=[CH:21][C:20]=2[O:28][CH3:29])[CH2:7][C:8]2[O:13]C(C)(C)[O:11][C:10](=O)[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(O)(C#CC2C(OC)=CN=C(CC)C=2)CC2OC(C)(C)OC(=O)C=2)CCCC1>>[CH:1]1([C:6]2([CH2:17][CH2:18][C:19]3[CH:24]=[C:23]([F:25])[C:22]([CH2:26][OH:27])=[CH:21][C:20]=3[O:28][CH3:29])[O:30][C:10](=[O:11])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 58764221HCID 58764221, compound

HCID 58764288HCID 58764288, compound

Product 1

HCID 58764145HCID 58764145, compound

Procedure

The desired product was prepared analogously to example A(2), where 6-[2-cyclopentyl-4-(5-fluoro-4-hydroxymethyl-2-methoxy-phenyl)-2-hydroxy-but-3-ynyl]-2,2 dimethyl-[1,3]dioxin-4-one (1.28 g, 3.03 mmol) was substituted in place 6-[2-Cyclopentyl-4-(2-ethyl-5-methoxy-pyridin-4-yl)-2-hydroxy-but-3-ynyl]-2,2-dimethyl-[1,3]dioxin-4-one. Yield: 1.4 g, 38%. 1H NMR (400 MHz, CDCl3) δ: 1.37-1.49 (1 H, m) 1.53-1.97 (9 H, m) 2.53-2.6 (1 H, m) 2.64-2.7 (1 H, m) 2.75 (2 H, s) 3.41 (2H, s) 3.79 (3 H, s) 4.71 (2 H, s) 6.79 (1 H, d, J=9.85 HZ) 6.87 (1 H, d, J=5.81 Hz). MS (ESI): 363 (M−H).

Sources & evidence

ORD record: ord-ecc5636ddbdd4910b29bde522c52c313
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268835B2

Reaction notes

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