Acetic Acid → HCID 57440192, compound

HRID 708548Notes

Reaction equation

HRID 708548 reaction equation
[Si]([O:18][CH2:19][C@@H:20]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Na+].C(O)(=O)C>CO.O>[OH:18][CH2:19][C@@H:20]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 131733855(S)-di-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)butane-1,3-diyl)dicarbamate

Product 1

HCID 57440192HCID 57440192, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (S)-di-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)butane-1,3-diyl)dicarbamate (6.25 g, 11.51 mmol) in MeOH (100 mL) was added sodium hydroxide (1.38 g, 34.5 mmol) in water (20.0 mL). The mixture was heated to 70° C. for 18 h then cooled to room temperature and partially concentrated in vacuo. DCM was then added and the mixture was cooled to 0° C., whereupon acetic acid (2.31 mL, 40.3 mmol) was added. The organic layer was then separated, washed with saturated NaHCO3 (aq) and brine. The combined aqueous portions were extracted with DCM and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-Heptane) to afford the title compound (1.67 g, 48%). LCMS: Rt=0.67 min, m/z=305.1 (M+1) Method 2m_acidic. 1H NMR (400 MHz, CDCl3) δ ppm 5.06 (br s, 1H) 4.83 (br s, 1H) 3.82-3.64 (m, 2H) 3.61 (dd, J=10.3, 4.9 Hz, 1H) 3.43-3.25 (m, 1H) 3.11-2.93 (m, 1H) 2.18 (br s, 1H) 1.79-1.65 (m, 1H) 1.64-1.58 (m, 1H) 1.51-1.36 (m, 18H).

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationpartially concentrated in vacuo
  3. additionDCM was then added
  4. additionwas added
  5. customThe organic layer was then separated
  6. washwashed with saturated NaHCO3 (aq) and brine
  7. extractionThe combined aqueous portions were extracted with DCM
  8. dry with materialthe combined organic layers were dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified via silica gel chromatography (EtOAc-Heptane)

Sources & evidence

ORD record
ord-3f4877c92254416f832c1cc95e6daa39
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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