Hydrochloric Acid → HCID 86702654, compound

HRID 62585Notes

Reaction equation

HRID 62585 reaction equation
C([O:5][C:6](=[O:53])[CH2:7][N:8]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH2:13][CH2:12][N:11]([CH2:25][CH:26]([NH:37][CH:38](C(OC(C)(C)C)=O)[C:39]([O:41]C(C)(C)C)=[O:40])[CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl.CC[O:57][CH2:58][CH3:59].[O:60]1CCOCC1>>[NH2:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][CH2:27][CH:26]([N:37]([CH2:59][C:58]([OH:57])=[O:60])[CH2:38][C:39]([OH:41])=[O:40])[CH2:25][N:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:6]([OH:53])=[O:5])[CH2:16][CH2:15][N:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][CH2:12]2)=[CH:31][CH:32]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 86702655{4-[5-(4-Aminophenyl)-2-(bis-tert-butoxycarbonylmethylamino) pentyl]-7-tert-butoxycarbo-nylmethyl-[1,4,7]-triazonan-1-yl}acetic acid tert-butyl ester

Product 1

HCID 86702654HCID 86702654, compoundYield 88%

Procedure

To a flask containing compound 7 (8.5 mg, 0.011 mmol) at 0-5° C. was added dropwise 4M HCl (g) in 1,4-dioxane (3 mL) over 20 min. The resulting mixture was gradually warmed to room temperature and continuously stirred for 18 h. Ether (20 mL) was added to the reaction mixture which was then stirred for 10 min. The resulting mixture was placed in the freezer for 1 h. The resulting precipitate was filtered and washed with ether. The solid product was quickly dissolved in deionized water. The aqueous solution was concentrated in vacuo to provide 8 (7.1 mg, 88%) as an off-white solid. 1H NMR (D2O, 300 MHz) δ 1.50-1.73 (m, 4H), 2.53-2.65 (m, 2H), 3.00-3.35 (m, 10H), 3.49-3.85 (m, 13H), 7.17-7.30 (m, 4H); 13C NMR (D2O, 300 MHz) δ 25.7 (t), 26.6 (t), 33.5 (t), 48.2 (t), 49.6 (t), 50.4 (t), 51.8 (t), 52.5 (t), 53.7 (t), 54.0 (t), 56.0 (t), 60.3 (d), 123.0 (d), 127.5 (s), 130.0 (d), 142.2 (s), 168.0 (s), 170.0 (s), 173.6 (s). HRMS (Positive ion FAB) Calcd for C25H40N5O8: [M+H]+ m/z 538.2877. Found: [M+H]+ m/z 538.2880.

Workup

  1. stirringwas then stirred for 10 min
  2. waitThe resulting mixture was placed in the freezer for 1 h
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ether
  5. dissolutionThe solid product was quickly dissolved in deionized water
  6. concentrationThe aqueous solution was concentrated in vacuo

Sources & evidence

ORD record
ord-99f86b9e67e147fe837aa95a14b023bf
Source dataset
uspto-grants-2016_09
Patent number
US09446995B2

Reaction notes

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