2-Oxazolidinone → HCID 58305317, compound

HRID 1805391Notes

Reaction equation

HRID 1805391 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C[O:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14](I)[CH:13]=[C:12](Br)[CH:11]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@:26]2([CH:38]([CH3:40])[CH3:39])[C@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:37])[CH2:27]2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C@@:26]2([CH:38]([CH3:40])[CH3:39])[C@@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([C:12]4[CH:11]=[C:10]([CH:15]=[C:14]([N:3]5[CH2:4][CH2:5][O:1][C:2]5=[O:6])[CH:13]=4)[C:9]([OH:8])=[O:18])[C:29]3=[O:37])[CH2:27]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 739492-OxazolidinoneHCID 21942573Methyl 3-bromo-5-iodobenzoateHCID 67233428HCID 67233428, compound

Product 1

HCID 58305317HCID 58305317, compound

Procedure

The title compound was prepared in analogy to Example 95 starting from oxazolidin-2-one, 3-bromo-5-iodobenzoic methylester (prepared as in Example 92), (1R,2R) and (1S,2S)-2-(4-chlorophenyl)-2-isopropylspiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 2. LC/MS m/e calcd. for C29H25ClN2O5: 516, observed (M+H)+: 517.2 1H NMR (400 MHz, DMSO-d6) δppm 0.77 (d, 3 H) 0.89 (d, 3 H) 2.16 (d, 1 H) 2.28 (d, 1 H) 2.95-3.02 (m, 1 H) 4.17-4.25 (m, 2 H) 4.40-4.58 (m, 2 H) 5.43 (d, 1 H) 6.65-6.76 (m, 1 H) 6.78-6.91 (m, 2 H) 7.11 (t, 1 H) 7.61 (d, 1 H) 7.69 (d, 1 H) 7.79 (s, 1 H) 7.92-8.03 (m, 2 H) 8.21 (s, 1 H) 13.44 (s, 1 H).

Sources & evidence

ORD record
ord-585bb3ac4d73409a9c3a948d66444838
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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