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

HRID 1805363Notes

Reaction equation

HRID 1805363 reaction equation
C[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]>>[O:15]=[C:11]1[N:10]([C:8]2[CH:9]=[C:4]([CH:5]=[C:6]([N:25]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C@:28]4([C:19]5([CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)[CH2:18]4)[C:26]3=[O:27])[CH:7]=2)[C:3]([OH:2])=[O:17])[CH2:14][CH2:13][O:12]1

Participants

4

Reactant 3

HCID 7054IsatinHCID 5489754-MethylideneoxaneHCID 67229228Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate

Product 1

HCID 58305302(S)-3-(2-oxo-1,3-oxazolidin-3-yl)-5-(2-oxo-2'',3'',5'',6''-tetrahydrodispiro[indole-3,1'-cyclopropane-2',4''-pyran]-1(2H)-yl)benzoic acid

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-methylene-tetrahydro-pyran, isatin (commercially available) according to Scheme 2. LC/MS m/e calcd. for C24H22N206: 434, observed (M+H)+: 434.21H NMR (400 MHz, DMSO-d6) δppm 1.72-1.80 (m, 1 H) 1.83 (d, J=4.29 Hz, 1 H) 1.91-2.01 (m, 3 H) 2.06-2.16 (m, 1 H) 3.36-3.44 (m, 1 H) 3.50-3.56 (m, 1 H) 3.58-3.65 (m, 2 H) 4.13-4.21 (m, 2 H) 4.48 (t, J=7.96 Hz, 2 H) 6.90 (d, J=8.08 Hz, 1 H) 7.07 (t, 1 H) 7.23 (t, 1 H) 7.29 (d, J=7.58 Hz, 1 H) 7.71 (s, 1H) 7.92 (s, 1 H) 8.19 (s, 1 H) 13.40 (s, 1 H).

Sources & evidence

ORD record
ord-ab4f3bf914a146ccab515d3efef0f085
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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