HCID 86678284, compound → HCID 86678285, compound

HRID 2407888Notes

Reaction equation

HRID 2407888 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][CH2:13][C@H:14]([CH3:70])[NH:15][C:16](=[O:69])[C@@H:17]([NH:51]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH2:18][S:19][CH2:20][C@H:21]([O:37][C:38](=[O:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:22][O:23][C:24](=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>N1CCCCC1.C1COCC1.C(OC)(C)(C)C.C(OCC)(=O)C>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][CH2:13][C@H:14]([CH3:70])[NH:15][C:16](=[O:69])[C@@H:17]([NH2:51])[CH2:18][S:19][CH2:20][C@H:21]([O:37][C:38](=[O:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:22][O:23][C:24](=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 1

HCID 86678284HCID 86678284, compound

Product 1

HCID 86678285HCID 86678285, compound

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 8082PiperidineSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

(6S,9R,13R)-9-(((9H-fluoren-9-yl)methoxy)carbonylamino)-13-(dodecanoyloxy)-6-methyl-8,16-dioxo-4,15-dioxa-11-thia-7-azaheptacosylphosphonic acid diethyl ester (1 eq, from the previous step) in was dissolved in 20% piperidine in THF (0.1 M) and stirred at room temperature for 2 hours. The viscous reaction mixture was diluted in methyl tert-butyl ether and ethyl acetate. The organic layer was washed with 1:1 saturated aqueous NH4Cl/water (2×), brine, dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-5% methanol in DCM to give the product.

Workup

  1. washThe organic layer was washed with 1:1 saturated aqueous NH4Cl/water (2×), brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated en vaccuo
  4. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  5. customto give the product

Sources & evidence

ORD record
ord-c5cafb3a491b46e99320798203d872e3
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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