Potassium Carbonate → (5R,9R)-tert-butyl 9-(dodecyloxy)-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylate

HRID 2205019Notes

Reaction equation

HRID 2205019 reaction equation
FC(F)(F)S(O[CH2:7][C@H:8]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=O)=O.[CH:38]1[C:50]2[CH:49]([CH2:51][O:52][C:53]([NH:55][C@@H:56]([CH2:64][SH:65])[C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[O:54])[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]=2[CH:41]=[CH:40][CH:39]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:24]([O:23][C@H:8]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:7][S:65][CH2:64][C@@H:56]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[NH:55][C:53](=[O:54])[O:52][CH2:51][CH:49]1[C:50]2[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=2[C:43]2[C:48]1=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11440950(R)-tert-Butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-mercaptopropanoateHCID 86678303(R)-2,3-bis(dodecyloxy)propyl trifluoromethanesulfonate

Product 1

HCID 71294734(5R,9R)-tert-butyl 9-(dodecyloxy)-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-2,3-bis(dodecyloxy)propyl trifluoromethanesulfonate (1 eq) in ethanol (0.15 M) was added (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-mercaptopropanoate (8, 1.5 eq) and potassium carbonate (1 eq). The reaction mixture was stirred at 60° C. for 30 minutes. The salt from the reaction was filtered off and the filtrate was concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-40% EtOAc/Hex to give the product.

Workup

  1. filtrationThe salt from the reaction was filtered off
  2. concentrationthe filtrate was concentrated en vaccuo
  3. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  4. customto give the product

Sources & evidence

ORD record
ord-573ea2e3ba6c4629bb0aa4d01585dac9
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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