Sodium Hydroxide → HCID 10781998, compound

HRID 2393780Notes

Reaction equation

HRID 2393780 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([CH2:9][C:10]([Cl:12])=[CH2:11])[C:5]([O:7][CH3:8])=[O:6].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:8][O:7][C:5](=[O:6])[C:4]([CH2:9][C:10]([Cl:12])=[CH2:11])([C:3]([O:2][CH3:1])=[O:13])[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 10726998HCID 10726998, compound

Product 1

HCID 10781998HCID 10781998, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

A mixture of the title compound of Example 2A (519.6 g, 2.564 mol) and tert-butyl bromoacetate (500 g, 2.564 mol) was added dropwise over 30 min to a stirred mixture of 10N aqueous NaOH (2.56 L, 25.6 mol) and benzyltriethylammonium chloride (2.56 g, 11.2 mmol) at 10°. The reaction mixture was stirred at room temperature for 2 h and then diluted with Hex (750 mL). The organic phase was separated and washed serially with H2O (100 mL) and brine (2×100 mL), dried (MgSO4), and concentrated under reduced pressure to give the title compound (822 g, 100% yield) which was used without further purification for the next step (Example 2C). 1H NMR (400 MHz, CDCl3) δ5.32 (d, J=1.4 Hz, 1H), 5.20 (broad s, 1H), 3.75 (s, 6H), 3.25 (broad s, 2H), 3.06 (s, 2H), 1.43 (s, 9H). MS (FAB) m/z 321 (MH+).

Workup

  1. additiondiluted with Hex (750 mL)
  2. customThe organic phase was separated
  3. washwashed serially with H2O (100 mL) and brine (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d509b3c6449427591362a2f3491e433
Source dataset
uspto-grants-1998_09
Patent number
US05808085

Reaction notes

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