Lithium Hydroxide → HCID 57978223, compound

HRID 1866556Notes

Reaction equation

HRID 1866556 reaction equation
[OH-].[Li+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:18][NH:19][C:20]([CH3:34])([CH3:33])[CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([O:31]C)=[O:30])[CH:25]=[CH:26][CH:27]=2)=[CH:13][C:12]=1[CH2:43][OH:44])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1.CO>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[CH2:18][NH:19][C:20]([CH3:34])([CH3:33])[CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([OH:31])=[O:30])[CH:25]=[CH:26][CH:27]=2)=[CH:13][C:12]=1[CH2:43][OH:44])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 70946581HCID 70946581, compound

Product 1

HCID 57978223HCID 57978223, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide solution (1M in water, 16.2 mL, 16.2 mmol) was added to a solution of methyl (3-{2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]-2-methylpropyl}phenyl)acetate (preparation 147), (4.80 g, 8.1 mmol) in tetrahydrofuran (49 mL) and methanol (17 mL) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo and the residue was diluted with water and acidified to pH 7 with 1M hydrochloric acid. The resulting precipitate was filtered off and washed with water to afford the title compound as a pale yellow solid in 94% yield, 4.37 g 1H NMR (400 MHz, DMSO-d6) δ: 7.45-7.38 (6H, m), 7.31 (2H, m), 7.13 (1H, m) 7.02 (3H, m), 5.04 (3H, m), 4.52 (2H, d), 3.52 (2H, d), 2.43 (2H, d), 3.37 (2H, d), 1.24 (6H, m), 0.78 (9H, s), 0.02 (3H, s), -0.92 (3H, s) ppm; LRMS ESI m/z 659 [M+H]+

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionthe residue was diluted with water
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-a46d721b497a4baeafe2470c67a5a0e8
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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