Hydrochloric Acid → HCID 57978199, compound

HRID 1866521Notes

Reaction equation

HRID 1866521 reaction equation
[OH:1][C@H:2]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][OH:26])[CH:19]=1)[CH2:3][NH:4][C@H:5]([CH3:17])[CH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12]C)=[O:11].[OH-].[Li+].Cl>O1CCCC1>[OH:1][C@H:2]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][OH:26])[CH:19]=1)[CH2:3][NH:4][C@H:5]([CH3:17])[CH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57978258HCID 57978258, compound

Product 1

HCID 57978199HCID 57978199, compoundYield 119.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]benzoate (Preparation 60) (5.12 g, 14.24 mmol) in tetrahydrofuran (35 ml), was added aqueous lithium hydroxide solution (1M, 29 ml, 29 mmol) and the solution left to stir at room temperature for 18 hours. Aqueous hydrochloric acid (1M, 29 ml, 29 mmol) was added and the tetrahydrofuran/water removed in vacuo to give the title compound as an off-white solid (5.87 g) that was used without further purification. 1H NMR (400 MHz, CD3OD): δ=7.86-7.84 (1H, d), 7.82 (1H, s), 7.37-7.30 (3H, m), 7.17-7.15 (1H, dd), 6.79-6.77 (1H, d), 4.89-4.85 (1H, m), 4.65 (2H, s), 3.60-3.50 (1H, m), 3.21-3.15 (3H, m), 2.84-2.78 (1H, dd), 1.25-1.23 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 346, [M+Na]+ 368, [M−H]− 344. CHN analysis: found C, 50.29; H, 6.07; N, 3.07. C19H23NO5+2.0LiCl+1.3H2O requires C, 50.31; H, 5.69; N, 3.09.

Workup

  1. waitthe solution left
  2. customthe tetrahydrofuran/water removed in vacuo

Sources & evidence

ORD record
ord-2b8bd4cd70c444079f14f12ed75ff218
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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