Carbon Dioxide → HCID 70171841, compound

HRID 2306265Notes

Reaction equation

HRID 2306265 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][C:16]2[N:17]=[CH:18][N:19]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:47](=[O:49])=[O:48].[CH:50]([Si:53](Cl)([CH:57]([CH3:59])[CH3:58])[CH:54]([CH3:56])[CH3:55])([CH3:52])[CH3:51]>C(Cl)Cl.O>[CH:50]([Si:53]([O:48][C:47](=[O:49])[N:13]([C@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)[CH2:14][CH2:15][C:16]1[N:17]=[CH:18][N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=1)([CH:57]([CH3:59])[CH3:58])[CH:54]([CH3:56])[CH3:55])([CH3:52])[CH3:51]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 70171855HCID 70171855, compound

Product 1

HCID 70171841HCID 70171841, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of (S)-1-(tert-butoxycarbonyl)-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine, as described above in Step E, (411 mg, 0.786 mmol) in CH2Cl2 (10 mL), was added triethylamine (0.110 mL, 0.786 mmol) and the mixture was cooled to −78° C. Solid CO2 (1.73 g, 39.3 mmol) was added and after 30 min, triisopropylsilyl chloride (0.172 mL, 0.802 mmol) was added and the reaction mixture was warmed to ambient temperature. After 1 hour, the reaction was diluted with water and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 3% MeOH—0.1% to 0.3% NH4OH, to yield the above-titled compound.

Workup

  1. temperaturethe reaction mixture was warmed to ambient temperature
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluting with a gradient of CH2Cl2—1% to 3% MeOH—0.1% to 0.3% NH4OH

Sources & evidence

ORD record
ord-13f465e105ee405c8737d79da3cc82d5
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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