ethyl {4-[(2'-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-1'(2'H)-yl)methyl]phenoxy}acetate → {4-[(2'-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-1'(2'H)-yl)methyl]phenoxy}acetic acid

HRID 422869Notes

Reaction equation

HRID 422869 reaction equation
[O:1]=[C:2]1[C:10]2([C:22]3[C:13](=[CH:14][C:15]4[O:20][CH2:19][CH2:18][O:17][C:16]=4[CH:21]=3)[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:26][CH:25]=1.O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1C=C(C=CC=1)OCC(OCC)=O>>[O:1]=[C:2]1[C:10]2([C:22]3[C:13](=[CH:14][C:15]4[O:20][CH2:19][CH2:18][O:17][C:16]=4[CH:21]=3)[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 45280338ethyl {4-[(2'-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-1'(2'H)-yl)methyl]phenoxy}acetateHCID 45280396HCID 45280396, compound

Product 1

HCID 45280339{4-[(2'-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-1'(2'H)-yl)methyl]phenoxy}acetic acid

Procedure

Following the procedure as described in EXAMPLE 15 and making non-critical variations using ethyl {4-[(2′-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-1′(2′H)-yl)methyl]phenoxy}acetate to replace ethyl {3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]phenoxy}acetate, {4-[(2′-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-1′(2′H)-yl)methyl]phenoxy}acetic acid was obtained (66%) as a colorless solid: mp 223-224° C.; 1H NMR (300 MHz, DMSO-d6) δ 13.00 (s, 1H), 7.31-7.22 (m, 3H), 7.18-7.13 (m, 1H), 7.05-6.98 (m, 2H), 6.92-6.85 (m, 2H), 6.53 (s, 1H), 6.08 (s, 1H), 4.93-4.77 (m, 3H), 4.70-4.61 (m, 3H), 4.21-4.08 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 180.6, 176.6, 170.1, 157.0, 154.7, 144.1, 142.1, 137.8, 131.7, 128.7, 128.5, 123.6, 123.0, 121.2, 114.6, 110.9, 109.4, 98.8, 79.4, 64.4, 64.2, 63.5, 57.2, 42.4; MS (ES+) m/z 459.9 (M+1).

Sources & evidence

ORD record
ord-413a734e6b3d406f9494df7811ede97d
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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