(R)-3-methoxydihydro-2H-pyran-4(3H)-one → ((3aS,5S,6aR)-5-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

HRID 1747156Notes

Reaction equation

HRID 1747156 reaction equation
[NH2:1][C@@H:2]1[CH2:9][C@H:5]2[O:6][CH2:7][CH2:8][C@@:4]2([C:10]([N:12]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)=[O:11])[CH2:3]1.[CH3:26][O:27][C@H:28]1[C:33](=O)[CH2:32][CH2:31][O:30][CH2:29]1>>[CH3:26][O:27][C@H:28]1[C@@H:33]([NH:1][C@@H:2]2[CH2:9][C@H:5]3[O:6][CH2:7][CH2:8][C@@:4]3([C:10]([N:12]3[CH2:17][C:16]4[CH:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=[CH:21][C:15]=4[O:14][CH2:13]3)=[O:11])[CH2:3]2)[CH2:32][CH2:31][O:30][CH2:29]1

Participants

3

Reactant 2

HCID 11320949(R)-3-methoxydihydro-2H-pyran-4(3H)-one2×HCID 86708156((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

Product 1

HCID 71768900((3aS,5S,6aR)-5-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

Procedure

The title compound was prepared from the reaction of the product of Step E and (R)-3-methoxydihydro-2H-pyran-4(3H)-one (Intermediate 1) following the procedure described in Example 1, Step H. 1H NMR (CHLOROFORM-d) δ: 7.42 (d, J=8.6 Hz, 1H), 7.36 (br. s., 1H), 6.95 (d, J=8.1 Hz, 1H), 5.43 (br. s., 2H), 4.96-5.11 (m, 1H), 4.82 (br. s., 2H), 3.84-4.15 (m, 3H), 3.68 (d, J=7.1 Hz, 1H), 3.55 (br. s., 1H), 3.32-3.45 (m, 4H), 3.20-3.32 (m, 2H), 2.69-2.84 (m, 1H), 2.39 (br. s., 1H), 2.12-2.25 (m, 2H), 1.99-2.12 (m, 1H), 1.78-1.99 (m, 1H), 1.46-1.78 (m, 4H). Calculated for C23H29F3N2O5: 471.2 (M+1). found: 471.2.

Sources & evidence

ORD record
ord-d80a0c0f256a40a0b1256eac555f997b
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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