Water → HCID 71622430, compound

HRID 1502216Notes

Reaction equation

HRID 1502216 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][N:14]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][O:64][C:65]1[CH:70]=[CH:69][C:68]([C:71]2[C:72]([CH3:98])=[C:73]([C:80]([C:82]3[CH:91]=[C:90]4[C:85]([C:86](=[O:97])[N:87]([CH2:93][C:94]([O-:96])=[O:95])[C:88](=[O:92])[NH:89]4)=[CH:84][CH:83]=3)=[O:81])[N:74]3[C:79]=2[CH:78]=[CH:77][CH:76]=[CH:75]3)=[CH:67][CH:66]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([CH3:58])=[C:29]([C:36]([C:38]3[CH:47]=[C:46]4[C:41]([C:42](=[O:57])[N:43]([CH2:49][C:50]([O:52]C(C)(C)C)=[O:51])[C:44](=[O:48])[NH:45]4)=[CH:40][CH:39]=3)=[O:37])[N:30]3[C:35]=2[CH:34]=[CH:33][CH:32]=[CH:31]3)=[CH:23][CH:22]=1.O>C(Cl)Cl.CO>[OH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][N:14]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][O:64][C:65]1[CH:70]=[CH:69][C:68]([C:71]2[C:72]([CH3:98])=[C:73]([C:80]([C:82]3[CH:91]=[C:90]4[C:85]([C:86](=[O:97])[N:87]([CH2:93][C:94]([OH:96])=[O:95])[C:88](=[O:92])[NH:89]4)=[CH:84][CH:83]=3)=[O:81])[N:74]3[C:79]=2[CH:78]=[CH:77][CH:76]=[CH:75]3)=[CH:67][CH:66]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([CH3:58])=[C:29]([C:36]([C:38]3[CH:47]=[C:46]4[C:41]([C:42](=[O:57])[N:43]([CH2:49][C:50]([OH:52])=[O:51])[C:44](=[O:48])[NH:45]4)=[CH:40][CH:39]=3)=[O:37])[N:30]3[C:35]=2[CH:34]=[CH:33][CH:32]=[CH:31]3)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 131734307HCID 131734307, compound

Product 1

HCID 71622430HCID 71622430, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Trifluoroacetic acid (0.44 g, 3.89 mmol) is added to the tert-butyl 2,2′-({[2-(2-hydroxyethoxy)ethyl]imino}bis[pentane-5,1-diyloxybenzene-4,1-diyl(2-methylindolizine-1,3-diyl)carbonyl(2,4-dioxo-1,4-dihydroquinazoline-7,3(2H)-diyl)])diacetate (0.50 g, 0.39 mmol) in suspension in 4 mL of a DCM/MeOH mixture (1/1). The solution is stirred for 8 h at ambient temperature. The reaction mixture is run into water. The precipitate formed is filtered off, washed with water then with ethanol, and dried under vacuum. Purification by preparative HPLC on Kromasil C18 10 μm reverse phase [A=H2O/(CH3COONH4 0.1 M) 90/10; B=CH3CN/(CH3COONH4 0.1 M) 90/10, gradient A/B: 70/30 to 56/44] gives 25 mg (5%) of a yellow powder.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed with water
  4. dry with materialwith ethanol, and dried under vacuum
  5. customPurification by preparative HPLC on Kromasil C18 10 μm reverse phase [A=H2O/(CH3COONH4 0.1 M) 90/10

Sources & evidence

ORD record
ord-1121ab3d2ce54b6cb11e5e8f78012d80
Source dataset
uspto-grants-2015_12
Patent number
US09206177B2

Reaction notes

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