Benzyloxyacetyl chloride → HCID 24772586, compound

HRID 1676847Notes

Reaction equation

HRID 1676847 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)=[O:4].C(=O)(O)[O-].[Na+].[CH2:21]([O:28][CH2:29][C:30](Cl)=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 3

HCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 58566935HCID 58566935, compound

Product 1

HCID 24772586HCID 24772586, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-amino-benzoic acid methoxycarbonylmethyl ester 6 (10 grams, 47.84 mmol) and sodium bicarbonate (8 grams, 95.23 mmol) in ethyl acetate (50 mL) at 0° C. is added benzyloxy acetyl chloride (12 grams, 65.04 mmol) drop wise. The reaction mixture is stirred at room temperature for 10 hours. The solids are filtered off, and the ethyl acetate layer is washed with 5% sodium bicarbonate solution (2×25 mL), water (2×25 mL), dried over sodium sulfate, and distilled to give crude 7, which can be purified via crystallized with a suitable solvent.

Workup

  1. filtrationThe solids are filtered off
  2. washthe ethyl acetate layer is washed with 5% sodium bicarbonate solution (2×25 mL), water (2×25 mL)
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled
  5. customto give crude 7, which
  6. customcan be purified
  7. customvia crystallized with a suitable solvent

Sources & evidence

ORD record
ord-b453ab7d53384658a574cbf329699ed2
Source dataset
uspto-grants-2011_08
Patent number
US08007526B2

Reaction notes

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