Benzyloxyacetyl chloride → HCID 54120377, compound

HRID 369157Notes

Reaction equation

HRID 369157 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C@@:7]([OH:13])([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:3][CH:2]=1.[CH2:20]([O:27][CH2:28][C:29](Cl)=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:1]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][C:4]([C@@:7]([O:13][C:29](=[O:30])[CH2:28][O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 177085Benzyloxyacetyl chlorideHCID 54086122HCID 54086122, compound

Product 1

HCID 54120377HCID 54120377, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a dry flask under argon, were mixed 1.3 g (5 mmol) of methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate, 1.7 mL (10 mmol) of 95% benzyloxyacetyl chloride and 6.1 mL of pyridine. The reaction stirred for 48 hours and was quenched by pouring into 100 mL of 10% aqueous HCl and 200 mL of ether. The ether fraction was separated and washed with 50 mL of 10% aqueous HCl, 50 mL of H2O, 2×50 mL of NaHCO3 solution, 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated. The product was purified over 250 g of SiO2 using initially EtOAc/hexanes (1/9) followed by EtOAc/hexanes (1.5/8.5) as eluant to yield 1.5 g (80% yield) of methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-(2-phenylmethoxyacetoyl)oxypropionate.

Workup

  1. customwas quenched
  2. additionby pouring into 100 mL of 10% aqueous HCl and 200 mL of ether
  3. customThe ether fraction was separated
  4. washwashed with 50 mL of 10% aqueous HCl, 50 mL of H2O, 2×50 mL of NaHCO3 solution, 50 mL of H2O, 50 mL of brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe product was purified over 250 g of SiO2 using initially EtOAc/hexanes (1/9)

Sources & evidence

ORD record
ord-bd22df02ed1b4e5c9638a0e2d6a38e89
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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