Diisopropylethylamine → HCID 15513864, compound

HRID 1106931Notes

Reaction equation

HRID 1106931 reaction equation
C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:25]([N:28]1[C@H:36]([C:37]([O-:39])=O)[CH2:35][C:34](=[O:40])[C:33]2[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=2[N:31]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:30](=[O:52])[C@H:29]1[CH2:53][C:54]12[CH2:63][CH:58]3[CH2:59][CH:60]([CH2:62][CH:56]([CH2:57]3)[CH2:55]1)[CH2:61]2)(=[O:27])[CH3:26].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:75]([O:82][C:83](=[O:86])[CH2:84][NH2:85])[C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:25]([N:28]1[C@H:36]([C:37]([NH:85][CH2:84][C:83]([O:82][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)=[O:86])=[O:39])[CH2:35][C:34](=[O:40])[C:33]2[CH:41]=[CH:42][CH:43]=[CH:44][C:32]=2[N:31]([CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:30](=[O:52])[C@H:29]1[CH2:53][C:54]12[CH2:63][CH:58]3[CH2:59][CH:60]([CH2:62][CH:56]([CH2:57]3)[CH2:55]1)[CH2:61]2)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 21968257HCID 21968257, compound

Product 1

HCID 15513864HCID 15513864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

PyBroP (233 mg, 0.5 mmol) was added to a solution of (3R,5S)-4-acetyl-3-(1-adamantyl)methyl-1-benzyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine-5-carboxylate (264 mg, 0.5 mmol), glycine benzyl ester p-toluenesulphonate (170 mg, 0.5 mmol) and diisopropylethylamine (260 μl, 1.5 mmol in dry DCM (5 ml). The reaction mixture was stirred at room temperature for 18 hours, diluted with DCM (20 ml), washed successively with 2N HCl solution (25 ml), brine (25 ml) and dried (MgSO4). Filtration an evaporation of the solvent gave the crude product (350 mg) which was purified by flash chromatography on silica gel with ethyl acetate-DCM (3:7) as eluant, affording the product as a colourless oil. (190 mg, 55%).

Workup

  1. washwashed successively with 2N HCl solution (25 ml), brine (25 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration
  4. customan evaporation of the solvent
  5. customgave the crude product (350 mg) which
  6. customwas purified by flash chromatography on silica gel with ethyl acetate-DCM (3:7) as eluant

Sources & evidence

ORD record
ord-b802341e51534aacb9094ce243d7ba13
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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