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Diisopropylcarbodiimide → 1-[3-(4-Methyl-4-methyldisulfanyl-pentanoylamino)-propyloxy]-3,5-bis-(hydroxymethyl)-benzene

HRID 1695312
Notes
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Reaction equation

HRID 1695312 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[C:8]([CH2:14][OH:15])[CH:7]=1.[CH3:16][C:17]([S:24][S:25][CH3:26])([CH3:23])[CH2:18][CH2:19][C:20](O)=[O:21].C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:16][C:17]([S:24][S:25][CH3:26])([CH3:23])[CH2:18][CH2:19][C:20]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[C:8]([CH2:14][OH:15])[CH:7]=1)=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 115646344-Methyl-4-(methyldisulfanyl)pentanoic acidHCID 575709321-(3-Amino-propyloxy)-3,5-bis-(hydroxymethyl)-benzene

Product 1

HCID 575709171-[3-(4-Methyl-4-methyldisulfanyl-pentanoylamino)-propyloxy]-3,5-bis-(hydroxymethyl)-benzeneYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-amino-propyloxy)-3,5-bis-(hydroxymethyl)-benzene (50 mg) in dimethylformamide (1 mL) was added 4-methyl-4-methyldisulfanyl-pentanoic acid (44 mg), N,N′-diisopropylcarbodiimide (35 mL) and 1-hydroxybenzotriazole hydrate (5.8 mg). After 15 h at room temperature, water was added to the reaction mixture and the aqueous solution was extracted twice with ethyl acetate. The combined organic solutions were washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Interchrom Puriflash 5 g column, SiOH 15-35 μm), eluted with methanol/dichloromethane, 5:95 to give 1-[3-(4-methyl-4-methyldisulfanyl-pentanoylamino)-propyloxy]-3,5-bis-(hydroxymethyl)-benzene (48 mg):

Workup

  1. extractionthe aqueous solution was extracted twice with ethyl acetate
  2. washThe combined organic solutions were washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo to a residue
  5. customThe residue was purified by silica gel chromatography (Interchrom Puriflash 5 g column, SiOH 15-35 μm)
  6. washeluted with methanol/dichloromethane, 5:95

Sources & evidence

ORD record
ord-4fd01d9b94d3461a923c3c3589789e1e
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163736B2

Reaction notes

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