Hydrochloric Acid → HCID 68778999, compound

HRID 517654Notes

Reaction equation

HRID 517654 reaction equation
C([O:5][C:6](=[O:59])[CH2:7][N:8]([CH2:51][C:52](=[O:58])[O:53]C(C)(C)C)[CH:9]([CH2:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=1)[CH2:10][N:11]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH2:19][CH2:18][N:17]([CH2:31][C:32]([O-:34])=[O:33])[CH2:16][CH2:15][N:14]([CH2:35][C:36]([O-:38])=[O:37])[CH2:13][CH2:12]1)(C)(C)C.Cl.CCOCC>O1CCOCC1>[C:52]([CH2:51][N:8]([CH2:7][C:6]([OH:59])=[O:5])[CH:9]([CH2:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=1)[CH2:10][N:11]1[CH2:12][CH2:13][N:14]([CH2:35][C:36]([OH:38])=[O:37])[CH2:15][CH2:16][N:17]([CH2:31][C:32]([OH:34])=[O:33])[CH2:18][CH2:19][N:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:21][CH2:22]1)([OH:58])=[O:53]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68780816HCID 68780816, compound

Product 1

HCID 68778999HCID 68778999, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 10 (77.0 mg, 0.081 mmol) at 0-5° C. was treated dropwise with 4M HCl(g) in 1,4-dioxane (15 mL) over 20 min. The resulting mixture was allowed to warm to room temperature. After 22 h, ether (˜20 mL) was added and continued to stir for 10 min. The resulting mixture was capped and placed in the freezer for 1 h. The solid formed was filtered, washed with ether, and quickly dissolved in DI water. Evaporation of the aqueous solution gave an off-white solid 3p-2C-DEPA (68.0 mg, 97%). 1H NMR (D2O, 300 MHz) δ 1.26-1.40 (m, 1H), 1.48-1.70 (m, 3H), 2.52-2.78 (m, 2H), 2.90-3.70 (m, 27H), 3.75-3.98 (m, 2H), 7.35 (d, J=8.3 Hz, 2H), 8.06 (d, J=8.2 Hz, 2H); 13C NMR (D2O, 300 MHz) δ 27.08 (t), 27.12 (t), 34.64 (t), 48.45 (t), 48.82 (t), 50.22 (t), 51.09 (t), 52.40 (t), 53.58 (t), 54.28 (t), 55.46 (t), 59.43 (d), 123.55 (d), 129.40 (d), 145.71 (s), 150.54 (s), 169.54 (s), 172.97 (s), 173.93 (s); HRMS (Positive ion FAB) Calcd for C29H45N6O12 [M+H]+ m/z 669.3095. Found: [M+]+ m/z 669.3086.

Workup

  1. customThe resulting mixture was capped
  2. waitplaced in the freezer for 1 h
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with ether
  6. dissolutionquickly dissolved in DI water
  7. customEvaporation of the aqueous solution
  8. customgave an off-white solid 3p-2C-DEPA (68.0 mg, 97%)

Sources & evidence

ORD record
ord-ea9901aa3fe44d51ae2654d57a0fa495
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

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