Lithium hydroxide, monohydrate → HCID 11319396, compound

HRID 349445Notes

Reaction equation

HRID 349445 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:33])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[N:20]=[N:21][N:22]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[N:23]=3)[CH:14]=2)=[CH:6][CH:5]=1.O.[OH-].[Li+]>O1CCCC1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:22]2[N:21]=[N:20][C:19]([C:15]3[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=3)[C:12]([NH:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:34])=[O:2])=[CH:9][CH:8]=3)=[O:33])=[N:23]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11422170HCID 11422170, compound

Product 1

HCID 11319396HCID 11319396, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester (0.065 g, 0.14 mmol) prepared in Example 1, Step (e) was diluted with aqueous tetrahydrofuran followed by the addition of lithium hydroxide monohydrate (0.018 g, 0.4 mmol). Following the experimental conditions described in (d) yielded the free acid (0.045 g, 71%)as a white solid. 1H NMR (DMSO-d6) δ 12.8 (bs, 1H), 9.4 (t, 1H), 8.5 (s, 1H), 8.2 (d, 1H), 8.0 (d, 1H), 7.9 (d, 2H), 7.7 (t, 1H), 7.4 (dd, 4H), 6.9 (d, 2H), 5.9 (s, 2H), 4.5 (d, 2H), 3.7 s, 3H) ppm. Mp 202–205° C.

Sources & evidence

ORD record
ord-8109cb81693f4f21a955015c6d2e385f
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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