Diisopropylethylamine → Methyl 4-[(6-Aminohexanoylamino)methyl]-2,6-dihydroxybenzoate Hydrochloride

HRID 1274531Notes

Reaction equation

HRID 1274531 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[CH:13]=[C:12]([OH:14])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:15])[CH:5]=1.C(N(CC)C(C)C)(C)C.C1(=O)N([O:30][C:31](=O)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37]C(OC(C)(C)C)=O)C(=O)CC1>CN(C)C=O>[ClH:1].[NH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:31]([NH:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:15])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:12]([OH:14])[CH:13]=1)=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5074016Boc-6-Ahx-OSuHCID 22556072Methyl 4-aminomethyl-2,6-dihydroxybenzoate hydrochloride

Product 1

HCID 22556098Methyl 4-[(6-Aminohexanoylamino)methyl]-2,6-dihydroxybenzoate Hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-(aminomethyl)-2,6-dihydroxybenzoate hydrochloride (1.50 grams, 6.4 mmoles) was suspended in anhydrous N,N-dimethylformamide (25 mL), and N,N-diisopropylethylamine (2.2 mL, 12.8 mmoles) was added, followed by N-tert-butoxycarbonyl-6-aminohexanoic acid succinimidyl ester (2.10 grams, 6.4 mmoles). The mixture was stirred under dry nitrogen for 4 hours, during which time all solids dissolved. The solvent was then evaporated to leave a light brown syrup, which was partitioned between ethyl acetate (70 mL) and 1 M aqueous hydrochloric acid (50 mL). The layers were separated, and the ethyl acetate solution was washed with saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered, and evaporated to an amorphous off-white solid.

Workup

  1. dissolutiondissolved
  2. customThe solvent was then evaporated
  3. customto leave a light brown syrup, which
  4. customwas partitioned between ethyl acetate (70 mL) and 1 M aqueous hydrochloric acid (50 mL)
  5. customThe layers were separated
  6. washthe ethyl acetate solution was washed with saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL)
  7. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated to an amorphous off-white solid

Sources & evidence

ORD record
ord-bac33ec6f5234850bc89bee4a1a90f28
Source dataset
uspto-grants-2000_12
Patent number
US06156884

Reaction notes

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