Hydrochloric Acid → HCID 67228799, compound

HRID 1844321Notes

Reaction equation

HRID 1844321 reaction equation
C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C@@:17]1([C:31]2([OH:35])[CH2:34][CH2:33][CH2:32]2)[CH2:21][CH2:20][C@@H:19]([NH:22][C@@H:23]2[C@H:28]([O:29][CH3:30])[CH2:27][O:26][CH2:25][CH2:24]2)[CH2:18]1)=[O:16])=O)(C)(C)C.[ClH:36]>O1CCOCC1.CO>[ClH:36].[ClH:36].[C@H:12]12[CH2:14][C@H:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[C:15]([C@@:17]1([C:31]2([OH:35])[CH2:34][CH2:33][CH2:32]2)[CH2:21][CH2:20][C@@H:19]([NH:22][C@@H:23]2[C@H:28]([O:29][CH3:30])[CH2:27][O:26][CH2:25][CH2:24]2)[CH2:18]1)=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67229292HCID 67229292, compound

Product 1

HCID 67228799HCID 67228799, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 312751,4-DioxaneSolvent

Procedure

To 902 mg (1.827 mmol) of 1,5-anhydro-3-{[(1R,3S)-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-3-(1-hydroxycyclobutyl)cyclopentyl]amino}-2,3-dideoxy-4-O-methyl-D-erythro-pentitol was added 10 mL of 4 M HCl in dioxane, and a few drops of methanol sufficient to give a clear solution. The solution was stirred at ambient temperature for 45 minutes, then concentrated under reduced pressure to give 973 mg of the intermediate salt as a foam. 1H NMR (400 MHz, MeOD) δ ppm 1.57-1.70 (m, 1H) 1.73-1.93 (m, 4H) 1.93-2.10 (m, 4H) 2.14-2.28 (m, 2H) 2.29-2.44 (m, 3H) 2.46-2.59 (m, 2H) 3.35-3.77 (m, 12H) 3.98 (dd, J=11.6, 4.4 Hz, 1H) 4.26 (d, J=13.3 Hz, 1H) 4.45 (s, 1H) 5.21 (br. s., 1H). LC-MS ES+ 394.2.

Workup

  1. customto give a clear solution
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-95df852a06f345479751c4545762c3e2
Source dataset
uspto-grants-2015_02
Patent number
US08946413B2

Reaction notes

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