Isatin → (S)-methyl-3-(2-oxo-1,3-oxazolidin-3-yl)-5-(2-oxo-2'',3'',5'',6''-tetrahydrodispiro[indole-3,1'-cyclopropane-2',4''-pyran]-1(2 H)-yl)benzoate

HRID 1805393Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])[CH:7]=[C:6](Br)[CH:5]=1.[CH2:18]=[C:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[NH:25]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28](=O)[C:26]1=[O:27]>>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:5]=[C:6]([N:25]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C@:28]3([C:19]4([CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH2:18]3)[C:26]2=[O:27])[CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])[CH:9]=1

Participants

Reactant 3

HCID 7054Isatin

HCID 5489754-Methylideneoxane

HCID 67229228Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate

Product 1

HCID 58305334(S)-methyl-3-(2-oxo-1,3-oxazolidin-3-yl)-5-(2-oxo-2'',3'',5'',6''-tetrahydrodispiro[indole-3,1'-cyclopropane-2',4''-pyran]-1(2 H)-yl)benzoate

Procedure

The title compound was prepared in analogy to Example 101 starting from methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate prepared as in Example 101, 4-methylenetetrahydro-2H-pyran, isatin (commercially available) according to Scheme 2. LC/MS m/e calcd. for C25H24ClN2O6: 448, observed (M+H)+: 449.21 1HNMR (400 MHz, DMSO-d6) δppm 1.72-1.81 (m, 1 H) 1.83 (d, J=4.55 Hz, 1 H) 1.92-1.99 (m, 3 H) 2.07-2.15 (m, 1 H) 3.38-3.47 (m, 1 H) 3.51-3.57 (m, 1 H) 3.57-3.66 (m, 2 H) 3.90 (s, 3 H) 4.16 (t, J=7.83 Hz, 2 H) 4.49 (t, J=7.83 Hz, 2 H) 6.90 (d, J=7.83 Hz, 1 H) 7.08 (t, J=7.58 Hz, 1 H) 7.23 (t, J=7.71 Hz, 1 H) 7.29 (d, J=7.58 Hz, 1 H) 7.74 (s, 1 H) 7.93 (s, 1 H) 8.24 (s, 1 H).

Sources & evidence

ORD record: ord-cb076e3f62874e24a2b80eee3611bb93
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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