Diisopropylethylamine → HCID 22733430, compound

HRID 2084564Notes

Reaction equation

HRID 2084564 reaction equation
C(N(C(C)C)C(C)C)C.Cl.[OH:11][C:12]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=1[NH2:14].[C:20]12([CH2:30][C:31](O)=[O:32])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2.CCCP(=O)=O>ClCCl>[C:20]12([CH2:30][C:31]([NH:14][C:13]3[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:12]=3[OH:11])=[O:32])[CH2:27][CH:26]3[CH2:25][CH:24]([CH2:23][CH:22]([CH2:28]3)[CH2:21]1)[CH2:29]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1232211-Adamantaneacetic acidHCID 134088224-Aminobenzene-1,3-diol hydrochlorideHCID 16167369Propylphosphoric anhydride

Product 1

HCID 22733430HCID 22733430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.05 ml of N-ethyl-diisopropylamine is added to a solution of 323 mg 2,4-dihydroxyaniline hydrochloride (formula V), 388 mg (adamantan-1-yl)acetic acid (formula R3COOH) and 1.2 ml of propylphosphonic anhydride (50% in ethyl acetate) in 20 ml of dry dichloromethane at 0°. The mixture obtained is stirred for about 18 hours at room temperature and the solvent is evaporated off. The residue is dissolved in 50 ml of ethyl acetate and extracted with 1 M aqueous hydrochloric acid, saturated aqueous NaHCO3 solution and brine. The organic layer is dried and the solvent is evaporated off. The title compound is obtained (m.p. 195-197°).

Workup

  1. customThe mixture obtained
  2. customthe solvent is evaporated off
  3. dissolutionThe residue is dissolved in 50 ml of ethyl acetate
  4. extractionextracted with 1 M aqueous hydrochloric acid, saturated aqueous NaHCO3 solution and brine
  5. customThe organic layer is dried
  6. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-fbc7cf62199347879c9a02f1e9cdb526
Source dataset
uspto-grants-2004_04
Patent number
US06716865B1

Reaction notes

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