Diisopropylethylamine → HCID 46185509, compound

HRID 561974Notes

Reaction equation

HRID 561974 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]([N:22]3[C:26](=[O:27])[C@@H:25]([CH2:28][C:29]([OH:31])=O)[NH:24][C:23]3=[O:32])[C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:33]([O:35][CH2:36][CH2:37][O:38][NH2:39])=[CH2:34].C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]([C@@H:13]([N:22]3[C:26](=[O:27])[C@@H:25]([CH2:28][C:29]([NH:39][O:38][CH2:37][CH2:36][O:35][CH:33]=[CH2:34])=[O:31])[NH:24][C:23]3=[O:32])[C@H:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:15])=[N:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 46185508HCID 46185508, compound

Product 1

HCID 46185509HCID 46185509, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ((R)-1-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-acetic acid; hydrochloride salt (114 mg, 0.21 mmol) (prepared as described in example 8), O-(2-vinyloxy-ethyl)-hydroxylamine (26 mg, 0.25 mmol) (prepared as described in WO 02/06213) and N,N-diisopropylethyl amine (0.11 mL, 0.63 mmol) in N,N-dimethylformamide (2 mL) was added O-benzotriazol-1-yl-N,N,N′,N′-bis(tetramethylene)uronium hexafluororophosphate (110 mg, 0.25 mmol). The reaction mixture was stirred for 1 hour at room temperature then diluted with ethyl acetate and the organic layer washed successively with saturated aqueous sodium carbonate then brine, dried over sodium sulfate, filtered, concentrated and the residue purified by chromatography over silica gel eluted with ethyl acetate to give 2-((R)-1-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-N-(2-vinyloxy-ethoxy)-acetamide (81 mg, 61%) as a solid. LC-MS: calcd for C27H28IN5O5 [M+H+] 630. Found 630.

Workup

  1. washthe organic layer washed successively with saturated aqueous sodium carbonate
  2. dry with materialbrine, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue purified by chromatography over silica gel
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-63f82ced8e1546dcb99931042574367b
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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