Hydrochloric Acid → HCID 68784642, compound

HRID 517661Notes

Reaction equation

HRID 517661 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([NH:56][CH2:57][C:58]([O:60]C(C)(C)C)=[O:59])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:55])[CH2:29][CH2:30][CH:31]([CH:33]3[C:49]4([CH3:50])[CH:36]([CH:37]5[CH:46]([CH2:47][CH:48]4[OH:51])[C:45]4([CH3:52])[CH:40]([CH2:41][CH:42]([OH:53])[CH2:43][CH2:44]4)[CH2:39][CH:38]5[OH:54])[CH2:35][CH2:34]3)[CH3:32])=[CH:23][CH:22]=2)[CH2:14][CH2:13][N:12]([CH2:65][C:66]([O:68]C(C)(C)C)=[O:67])[CH2:11][CH2:10]1)=[O:7])(C)(C)C.Cl.CCOCC>O1CCOCC1>[C:6]([CH2:8][N:9]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([NH:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:55])[CH2:29][CH2:30][CH:31]([CH:33]3[C:49]4([CH3:50])[CH:36]([CH:37]5[CH:46]([CH2:47][CH:48]4[OH:51])[C:45]4([CH3:52])[CH:40]([CH2:41][CH:42]([OH:53])[CH2:43][CH2:44]4)[CH2:39][CH:38]5[OH:54])[CH2:35][CH2:34]3)[CH3:32])=[CH:23][CH:22]=2)[CH2:14][CH2:13][N:12]([CH2:65][C:66]([OH:68])=[O:67])[CH2:11][CH2:10]1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 72341761HCID 72341761, compound

Product 1

HCID 68784642HCID 68784642, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Compound 3 (20 mg, 0.02 mmol) in a ice-bath was added 4M HCl in 1,4-dioxane (5 mL). After the addition, the reaction mixture was gradually increased to room temperature and stirred for 24 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), immediately dissolved in H2O and CH3OH, and lypophilized to provide pure Compound 4 as a light brownish solid (19 mg, 97%). 1H NMR (CD3OD) 0.71 (s, 3H), 0.58-0.95 (m, 6H), 0.96-1.17 (m, 5H), 1.21-2.05 (m, 26H), 2.10-2.52 (m, 5H), 2.55-3.09 (m, 4H), 3.15-4.12 (m, 10H), 7.27 (d, 2H), 7.56 (d, 2H). HRMS (Positive ion FAB) Calcd for C45H72N5O10 [M+H]+ m/z 842.5279. Found: [M+H]+ m/z 842.5265.

Workup

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

Sources & evidence

ORD record
ord-0b58f1b525b4481bafccfdc0677877c0
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

Loading…