Diisopropylethylamine → HCID 18391857, compound

HRID 617761Notes

Reaction equation

HRID 617761 reaction equation
[CH2:1]([C:3]1([CH2:33][CH3:34])[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([NH:16][CH3:17])[CH3:15])=[CH:10][CH:9]=2)[N:5]([C:18]([NH:20][C@H:21]([CH2:29][CH2:30][CH3:31])[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[O:19])[C:4]1=[O:32])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:44][O:45][CH2:46][C:47](Cl)=[O:48]>C(Cl)Cl>[CH2:33]([C:3]1([CH2:1][CH3:2])[C@H:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([C@@H:14]([N:16]([CH3:17])[C:47](=[O:48])[CH2:46][O:45][CH3:44])[CH3:15])=[CH:12][CH:13]=2)[N:5]([C:18]([NH:20][C@H:21]([CH2:29][CH2:30][CH3:31])[C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)=[O:19])[C:4]1=[O:32])[CH3:34]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 18391856HCID 18391856, compound

Product 1

HCID 18391857HCID 18391857, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The residue from Step B was taken up in methylene chloride (150 mL) and cooled in an ice bath and diisopropylethylamine (7.0 mL, 40 mmol) was added. A solution of methoxyacetyl chloride (3.5 gm, 32 mmol) in methylene chloride (20 mL) was added over 10 min. The reaction was stirred another 15 min before it was quenched into a mixture of ice water, 2N hydrochloric acid (40 mL) and methylene chloride. The layers were separated and the aqueous layer was extracted with another portion of methylene chloride. The methylene chloride layers were each washed with brine, combined, dried over sodium sulfate and evaporated. The residue was purified by preparative chromatography with 5% methanol/25% ethyl acetate/70% hexanes to give 28 gm (97%) of the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. customwas quenched into a mixture of ice water, 2N hydrochloric acid (40 mL) and methylene chloride
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with another portion of methylene chloride
  5. washeach washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified by preparative chromatography with 5% methanol/25% ethyl acetate/70% hexanes

Sources & evidence

ORD record
ord-8a40abcaedc54bb0bdbfc81069e75ae1
Source dataset
uspto-grants-1999_09
Patent number
US05952321

Reaction notes

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