Hydrochloric Acid → (3-{(2R)-2-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-acetic acid

HRID 1866498Notes

Reaction equation

HRID 1866498 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][C@H:12]([NH:14][CH2:15][C@H:16]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=2)[CH3:13])[CH:6]=1.[OH-].[Li+].Cl>O1CCCC1>[Si:27]([O: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@H:12]([CH3:13])[CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:34])=[O:2])[CH:10]=[CH:9][CH:8]=1)([C:30]([CH3:33])([CH3:31])[CH3:32])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58959781methyl (3-{(2R)-2-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-acetate

Product 1

HCID 58959819(3-{(2R)-2-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl(3-{(2R)-2-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-acetate (Preparation 21) (7.04 g, 14.43 mmol) in tetrahydrofuran (40 ml) was treated with lithium hydroxide (28.9 ml of a 1M aqueous solution, 28.9 mmol) and the reaction left to stir at room temperature for 16 hours. Hydrochloric acid (28.9 ml of a 1M aqueous solution, 28.9 mmol) was added and then the tetrahydrofuran was removed in vacuo. The remaining aqueous layer was decanted and the residue washed with further water (10 ml). The residue was redisolved in methanol (30 ml) and the solvent removed in vacuo to give the title compound as a colorless foam (5.95 g) which was used without further purification. 1H NMR (400 MHz, CD3OD): δ=7.32 (1H, s), 7.25-7.18 (2H, m), 7.13 (1H, s), 7.12-7.10 (1H, d), 7.02-7.01 (1H, d), 6.79-6.77 (1H, d), 4.98-4.95 (1H, m), 4.65-4.64 (2H, d), 3.48 (2H, s), 3.48-3.43 (1H, m), 3.28-3.23 (1H, dd), 3.13-3.09 (1H, dd), 2.98-2.93 (1H, dd), 2.77-2.72 (1H, dd), 1.23-1.21 (3H, d), 0.86 (9H, s), 0.06 (3H, s), −0.13 (3H, s) ppm. LRMS (electrospray): m/z [M+H]+ 474, [M+Na]+ 496, [M−H]− 472. CHN analysis: found C, 64.15%; H, 8.25%; N, 2.84%. C26H39NO5Si+0.7H2O requires C 64.22%, H 8.37%, N 2.88%.

Workup

  1. waitleft
  2. customthe tetrahydrofuran was removed in vacuo
  3. customThe remaining aqueous layer was decanted
  4. washthe residue washed with further water (10 ml)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1783efed3c7b45d498455c30a94340af
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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