Lithium Hydroxide → HCID 57978338, compound

HRID 1866548Notes

Reaction equation

HRID 1866548 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14][CH2:15][CH:16]([OH:26])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=2)([CH3:13])[CH3:12])[CH:5]=1.[OH-].[Li+]>O1CCCC1.O>[OH:26][C@H:16]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=1)[CH2:15][NH:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:27])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69026936HCID 69026936, compound

Product 1

HCID 57978338HCID 57978338, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-{2-[2-hydroxy-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-2-methylpropyl}-benzoic acid methyl ester (preparation 139) (2.35 g, 6.32 mmol) and lithium hydroxide (303 mg, 12.64 mmol) in tetrahydrofuran (20 mL) and water (20 mL) was stirred at room temperature for 3 days. The reaction mixture was then concentrated in vacuo and the residue was diluted with water and acidified with 1M hydrochloric acid (12 mL). The mixture was stirred for 2 hours at room temperature and was then concentrated in vacuo. The crude residue was used in subsequent reactions without further purification. 1H NMR (400 MHz, CD3OD) δ: 7.87 (1H, m), 7.84 (1H, bs), 7.39-7.31 (3H, m), 7.19 (1H, dd), 6.79 (1H, d), 4.86 (1H, m), 4.66 (2H, s), 3.22-3.11 (2H, m), 3.02 (2H, m), 1.32 (6H, s) ppm; LRMS ESI m/z 360 [M+H]+

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionthe residue was diluted with water
  3. stirringThe mixture was stirred for 2 hours at room temperature
  4. concentrationwas then concentrated in vacuo
  5. customThe crude residue was used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-b725e5938aff4e3b882307b3a39afa93
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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