1-Hydroxybenzotriazole hydrate → HCID 178471441, compound

HRID 1666985Notes

Reaction equation

HRID 1666985 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:24]1[N:25]=[CH:26][N:27](S(C2C=CC(C)=CC=2)(=O)=O)[CH:28]=1)([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:24]1[N:25]=[CH:26][NH:27][CH:28]=1)([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 27960291-Hydroxybenzotriazole hydrateHCID 67444839Diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]malonate

Product 1

HCID 178471441HCID 178471441, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.2 g (7.61 mmol) of diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]malonate were dissolved in 190 ml of methanol and stirred with 4.66 g (30.45 mmol) of 1-hydroxybenzotriazole hydrate at RT for 1 h. The reaction mixture was concentrated under reduced pressure, and the residue was chromatographed on silica gel (CH2Cl2:MeOH 9:1). The product-containing fractions were concentrated and the oil obtained was dissolved in ethyl acetate and washed with saturated NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated. This gave 2.14 g (71%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was chromatographed on silica gel (CH2Cl2:MeOH 9:1)
  3. concentrationThe product-containing fractions were concentrated
  4. customthe oil obtained
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8d0d55b287094850bb061693dc26f62a
Source dataset
uspto-grants-2011_10
Patent number
US08044208B2

Reaction notes

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