18-Crown-6 → HCID 131714464, compound

HRID 638090Notes

Reaction equation

HRID 638090 reaction equation
[F-].[K+].[O:3]1CCOCCOCCOCCOCCOCC1.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][CH:31]2[NH:37][C:36](=[O:38])[C:35]3[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=3[N:33]3[C:43](=[O:51])[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=4[N:50]=[C:32]23)=[CH:22]1.[N+](C1C=CC([C@@:61]([NH:69][C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])([CH2:65][CH:66]([CH3:68])[CH3:67])[C:62]([O-])=[O:63])=CC=1)([O-])=[O:53].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(#N)C>[OH2:3].[CH3:75][C:73]([CH3:76])([O:72][C:70]([NH:69][C@@H:61]([CH2:65][CH:66]([CH3:67])[CH3:68])[C:62]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][CH:31]2[NH:37][C:36](=[O:38])[C:35]3[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=3[N:33]3[C:43](=[O:51])[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=4[N:50]=[C:32]23)=[CH:22]1)=[O:63])=[O:71])[CH3:74].[OH2:53].[OH2:3].[CH3:75][C:73]([CH3:76])([O:72][C:70]([NH:69][C@@H:61]([CH2:65][CH:66]([CH3:67])[CH3:68])[C:62]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][CH:31]2[NH:37][C:36](=[O:38])[C:35]3[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=3[N:33]3[C:43](=[O:51])[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=4[N:50]=[C:32]23)=[CH:22]1)=[O:63])=[O:71])[CH3:74]

Participants

8

Reactant 5

HCID 2855718-Crown-6HCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 13603553HCID 13603553, compoundHCID 70351890HCID 70351890, compound

Product 1

HCID 131714464HCID 131714464, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Potassium fluoride (117 mg, 2.02 mmole) was added to 10 ml of dry acetonitrile containing 1,4,7,10,13,16-hexaoxacyclooctadecane (266 mg, 1.01 mmole). To this solution were added 7-[(1H-indol-3-yl)methyl]quinazolino-(3,2-A)-1,4-benzodiazepin-5,13-(6H,7H)-dione (492 mg, 1.01 mmole), p-nitrophenyl-2(S)-((1,1-dimethyl)ethoxycarbonyl)amino-4-methylpentanoate (441 mg, 1.25 mmole) and 218 μl (1.25 mmole) of diisopropylethylamine under nitrogen. The reaction mixture was stirred rapidly, 10 ml of dimethylformamide was added, and one equivalent of each of the above reagents was added. After 60 hours, the reaction mixture was partitioned between ethyl acetate and water; the phases were separated and the organic layer was washed in succession with saturated sodium bicarbonate solution, 10% citric acid solution, and brine. Rotoevaporation of the dried (MgSO4) extracts gave a solid which was purified by silica gel chromatography (1:1 hexaneethyl acetate v/v).

Workup

  1. additionone equivalent of each of the above reagents was added
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. customthe phases were separated
  4. washthe organic layer was washed in succession with saturated sodium bicarbonate solution, 10% citric acid solution, and brine
  5. dry with materialRotoevaporation of the dried (MgSO4)
  6. customextracts gave a solid which
  7. customwas purified by silica gel chromatography (1:1 hexaneethyl acetate v/v)

Sources & evidence

ORD record
ord-d7fc44784d2548e4a2e70b39151ef986
Source dataset
uspto-grants-1985_12
Patent number
US04559339

Reaction notes

Loading…