Hydrochloric Acid → HCID 11091658, compound

HRID 850598Notes

Reaction equation

HRID 850598 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:41])[CH2:6][C@H:7]([NH:17][CH2:18][CH2:19][N:20](C(OC(C)(C)C)=O)[CH2:21][CH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[CH2:30][CH2:29][CH2:28][NH:27][C:26]=2[N:25]=1)[C:8]1[CH:16]=[CH:15][C:11]2[CH2:12][CH2:13][O:14][C:10]=2[CH:9]=1)[CH3:3]>O1CCOCC1>[CH2:2]([O:4][C:5](=[O:41])[CH2:6][C@@H:7]([C:8]1[CH:16]=[CH:15][C:11]2[CH2:12][CH2:13][O:14][C:10]=2[CH:9]=1)[NH:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[CH2:30][CH2:29][CH2:28][NH:27][C:26]=2[N:25]=1)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10951784HCID 10951784, compound

Product 1

HCID 11091658HCID 11091658, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl gas was rapidly bubbled through a solution of 2-10 (4.0 g, 7.2 mmol) in dioxane (160 ml) at 0° C. for 10 minutes. After 30 minutes, the solution was purged with argon for 30 minutes. The solution was concentrated to give the amine 2-11 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.91 (s, 1H), 7.40 (d, J=7.0 Hz, 1H), 7.23 (d, J=7.6 Hz, 1H), 7.10 (m,2H), 6.56 (d, J=6.1 Hz, 1H), 4.58 (m, 2H), 4.04 (m,2H), 3.49 (m, 4H), 3.19 (m, 4H), 2.90 (m, 2H), 2.79 (m, 2H), 2.30 (m, 2H), 1.98(m, 2H), 1.85 (m, 5H), 1.15 (t, J=7.1 Hz, 3H).

Workup

  1. customthe solution was purged with argon for 30 minutes
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-9c082dc9e1644f75948f27b08b12d593
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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