Hydrochloric Acid → HCID 74927732, compound

HRID 517663Notes

Reaction equation

HRID 517663 reaction equation
C([O:5][C:6](=[O:71])[CH2:7][N:8]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([NH:54][CH2:55][C:56]([O:58]C(C)(C)C)=[O:57])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:53])[CH2:28][CH2:29][CH:30]([CH:32]3[C:48]4([CH3:49])[CH:35]([CH:36]5[CH:45]([CH2:46][CH:47]4[OH:50])[C:44]4([CH3:51])[CH:39]([CH2:40][CH:41]([OH:52])[CH2:42][CH2:43]4)[CH2:38][CH2:37]5)[CH2:34][CH2:33]3)[CH3:31])=[CH:22][CH:21]=2)[CH2:13][CH2:12][N:11]([CH2:63][C:64]([O:66]C(C)(C)C)=[O:65])[CH2:10][CH2:9]1)(C)(C)C.Cl.CCOCC>O1CCOCC1>[C:6]([CH2:7][N:8]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([NH:54][CH2:55][C:56]([OH:58])=[O:57])[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:53])[CH2:28][CH2:29][CH:30]([CH:32]3[C:48]4([CH3:49])[CH:35]([CH:36]5[CH:45]([CH2:46][CH:47]4[OH:50])[C:44]4([CH3:51])[CH:39]([CH2:40][CH:41]([OH:52])[CH2:42][CH2:43]4)[CH2:38][CH2:37]5)[CH2:34][CH2:33]3)[CH3:31])=[CH:24][CH:25]=2)[CH2:13][CH2:12][N:11]([CH2:63][C:64]([OH:66])=[O:65])[CH2:10][CH2:9]1)([OH:71])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86649150HCID 86649150, compound

Product 1

HCID 74927732HCID 74927732, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of Compound 8 (20 mg, 0.02 mmol) in 1,4 dioxane (1 mL) was dropwise added 4M HCl in 1,4-dioxane (1 mL) at 0-5° C. After the addition, the reaction mixture was gradually increased to room temperature and stirred for 1.8 h. To this solution, ether (30 mL) was added and continuously stirred for 30 min. The resulting mixture was placed in the freezer for 2 h. Solid residue was quickly filtered, washed with ethyl ether (5 mL), and immediately dissolved in DI H2O and lypophilized to provide pure DCA-NE3TA as a light brownish solid (19 mg, 98%). 1H NMR (CD3OD) 0.71 (s, 3H), 0.92-3.90 (m, 55H), 3.97 (s, 1H), 4.09 (s, 1H), 7.28 (d, 2H), 7.57 (d, 2H); 13C NMR (CD3OD) 11.86, 16.39, 22.35, 23.50, 26.09, 27.02, 27.33, 28.53, 29.68, 31.79, 33.43, 33.63, 33.73, 33.91, 35.04, 35.55, 35.79, 36.05, 42.21, 44.44, 46.17, 71.16, 72.65, 120.41, 129.55, 130.54, 167.99, 173.96 HRMS (Positive ion FAB) Calcd for C45H72N5O9 [M+H]+ m/z 826.5330. Found: [M+H]+ m/z 826.5355.

Workup

  1. customat 0-5° C
  2. additionAfter the addition
  3. stirringcontinuously stirred for 30 min
  4. waitThe resulting mixture was placed in the freezer for 2 h
  5. filtrationSolid residue was quickly filtered
  6. washwashed with ethyl ether (5 mL)
  7. dissolutionimmediately dissolved in DI H2O

Sources & evidence

ORD record
ord-87c0a67d49164c4dbeb28ee972112e98
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

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