Hydrochloric Acid → HCID 24829229, compound

HRID 517660Notes

Reaction equation

HRID 517660 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([NH:40][CH2:41][C:42]([O:44]C(C)(C)C)=[O:43])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]3[C:33]4=[N:34][O:35][N:36]=[C:32]4[C:31]([N+:37]([O-:39])=[O:38])=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)[CH2:14][CH2:13][N:12]([CH2:49][C:50]([O:52]C(C)(C)C)=[O:51])[CH2:11][CH2:10]1)=[O:7])(C)(C)C.Cl.CCOCC>O1CCOCC1>[C:50]([CH2:49][N:12]1[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([NH:40][CH2:41][C:42]([OH:44])=[O:43])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]3[C:33]4=[N:34][O:35][N:36]=[C:32]4[C:31]([N+:37]([O-:39])=[O:38])=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)[CH2:16][CH2:17][N:9]([CH2:8][C:6]([OH:7])=[O:5])[CH2:10][CH2:11]1)([OH:52])=[O:51]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 16733248HCID 16733248, compound

Product 1

HCID 24829229HCID 24829229, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of Compound 16 (15.7 mg, 0.02 mmol) in 1,4-dioxane (1 mL) at 0-5° C. was added 4M HCl(g) in 1,4-dioxane (1 mL) dropwise over ˜15 min. The resulting mixture was allowed to warm to room temperature. Ether (˜15 mL) was added to the reaction mixture and stirred for 10 min. The resulting mixture was placed in the freezer for 1 h. The solid residue was filtered and washed with ether and quickly dissolved in 18μΩ deionized water. Evaporation of the aqueous solution gave pure Compound 17 (12.4 mg, 90%) as an orange solid. 1H NMR (CD3OD) δ 2.82-3.48 (m, 13H), 3.78-4.08 (m, 10H), 6.76 (d, 1H), 7.40-7.55 (m, 4H), 8.51 (d, 1H). HRMS (Positive ion FAB) Calcd for C27H34N8O9 [M+H]+ m/z 615.2527. Found: [M+H]+ m/z 615.2520. Analytical HPLC (tR=3.6 min, Method 2).

Workup

  1. waitThe resulting mixture was placed in the freezer for 1 h
  2. filtrationThe solid residue was filtered
  3. washwashed with ether
  4. dissolutionquickly dissolved in 18μΩ
  5. customEvaporation of the aqueous solution

Sources & evidence

ORD record
ord-1230ec3174db4315a70d1534c7fe0708
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

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