Sodium Hydroxide → HCID 68823217, compound

HRID 490043Notes

Reaction equation

HRID 490043 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[O:8][CH:9]([CH:25]([CH:32]2[CH2:36][O:35][C:34]([CH3:38])([CH3:37])[O:33]2)[O:26][CH2:27][C:28]([O:30]C)=[O:29])[CH:10]([NH:21][C:22](=[O:24])[CH3:23])[CH:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:12]=1)=[O:6]>C1COCC1>[C:22]([NH:21][CH:10]1[CH:9]([CH:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])[CH:32]2[CH2:36][O:35][C:34]([CH3:37])([CH3:38])[O:33]2)[O:8][C:7]([C:5]([OH:6])=[O:4])=[CH:12][CH:11]1[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57673673HCID 57673673, compound

Product 1

HCID 68823217HCID 68823217, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (5 mL, 0.1 M, 0.5 mmol) was added slowly to a stirred solution of 28 (100 mg, 0.19 mmol) in THF (5 mL). The resulting mixture was stirred for 2 h at room temperature. The organic solvent was evaporated and the aqueous solution was acidified with HCl to pH=2, extracted with ethyl acetate, and extract was concentrated to give 29 as a white solid (66 mg, 70%). mp 130° C. [α]D26+35.1° (c 1.2, CH3OH). 1H NMR (CD3OD, 500 MHz) 60.11 (s, 3H, CH3), 0.14 (s, 3H, CH3), 0.91 (s, 9H, 3CH3), 1.32 (s, 3H, CH3), 1.39 (s, 3H, CH3), 2.0 (s, 3H, NAc), 3.66 (s, 2H, OCH2), 3.98 (m, 2H), 4.14 (t, J=8.0 Hz, 1H), 4.20 (t, J=8.0 Hz, 1H), 4.27 (m, 1H, H-6), 4.33 (m, 1H), 4.63 (m, 1H, H-4), 5.84 (s, 1H, H-3). 13C NMR (CD3OD, 125 MHz) δ −4.65, −4.45, 18.81, 23.19, 25.43, 26.18, 26.61, 30.89, 51.97, 66.47, 68.13, 68.79, 70.76, 77.71, 78.38, 78.68, 109.35, 113.37, 144.93, 164.97, 173.24, 173.61. ESIMS calcd for C22H37NO10SiNa [M+Na]+ 526.3. Found 526.3. Anal. Calc. for C22H37NO10Si: C, 52.47; H, 7.41; N, 2.78. Found: C, 52.38; H, 7.48; N, 2.64.

Workup

  1. customThe organic solvent was evaporated
  2. extractionextracted with ethyl acetate
  3. extractionextract
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-ac346403013a4ddfade5349ce4dae4a4
Source dataset
uspto-grants-2009_05
Patent number
US07527934B2

Reaction notes

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