Hydrochloric Acid → HCID 18922495, compound

HRID 1289971Notes

Reaction equation

HRID 1289971 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 5200412Methyl 5-Amino-2-chlorobenzoate

Product 1

HCID 18922495HCID 18922495, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Step A was taken up in 100 mL of methylene chloride and cooled in an ice bath. To the solution was added 7.6 mL of benzyl chloroformate and after 5 min 20 mL of DIPEA was added dropwise over 5 min. After stirring at r.t. for 3 h, the reaction was poured into water containing 50 mL of 2N HCl and was extracted twice with methylene chloride. The organics were washed with a portion of brine, combined, dried over sodium sulfate and evaporated to give a solid. This was triturated with hot 5% ethyl acetate in hexanes, cooled, filtered and air dried to afford 16.5 g of title compound as an off white solid. T.l.c. (30% ethyl acetate in hexanes) Rf =0.75

Workup

  1. temperaturecooled in an ice bath
  2. extractionwas extracted twice with methylene chloride
  3. washThe organics were washed with a portion of brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give a solid
  7. customThis was triturated with hot 5% ethyl acetate in hexanes
  8. temperaturecooled
  9. filtrationfiltered
  10. customair dried

Sources & evidence

ORD record
ord-de7d73d650004740bc5f28316c40a2bb
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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