Acetic Acid → HCID 69655025, compound

HRID 1794837Notes

Reaction equation

HRID 1794837 reaction equation
C([O:3][C:4](=[O:35])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][CH2:20][C@H:21]([OH:34])[C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:23]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)C.[OH-].[Na+].C(O)(=O)C>C(O)C>[OH:34][C@H:21]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([NH:29][S:30]([CH3:33])(=[O:31])=[O:32])[CH:23]=1)[CH2:20][NH:19][CH:16]1[CH2:17][CH2:18][N:13]([C:10]2[CH:9]=[CH:8][C:7](/[CH:6]=[CH:5]/[C:4]([OH:35])=[O:3])=[CH:12][CH:11]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 21021937HCID 21021937, compound

Product 1

HCID 69655025HCID 69655025, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.10 g (0.2 mmol) of (E)-3-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-phenyl)-acrylic acid ethyl ester (which was obtained in Example 183) in ethanol (3 mL) was treated with 3 mL of 1 N NaOH. After 18 h at room temperature, the mixture was acidified with acetic acid. The resulting suspension was filtered and the precipitate was washed with water, and dried in vacuo to give 0.09 g of a tan solid; m.p. 220° C.; 1H NMR (DMSO-d6) δ 1.20–1.40 (m, 2 H), 1.80–1.95 (m, 2 H), 2.57–2.95 (m, 5 H), 2.92 (t, 3 H), 3.74–3.82 (m, 2 H), 4.48–4.52 (m, 1 H), 6.22 (s, 1 H), 6.27 (s, 1 H), 6.81–7.03 (m, 4 H), 7.18 (d, 1 H), 7.42–7.49 (m, 3 H)); MS (ES) m/z: 476.0 (MH+).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe precipitate was washed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-7ba43c1d82ac448cb0d224f2e64bdcb4
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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