Hydrochloric Acid → HCID 136384756, compound

HRID 494575Notes

Reaction equation

HRID 494575 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][C:5]1([CH3:37])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26]C(=O)OC(C)(C)C)=[CH:25][C:19]=3[S:18](=[O:35])(=[O:34])[N:17]=2)[C:6]1=[O:36].[ClH:40]>O1CCOCC1>[Cl:40][NH:26][C:24]1[CH:23]=[CH:22][C:20]2[NH:21][C:16]([C:7]3[C:6](=[O:36])[C:5]([CH2:4][CH2:3][C:2]([CH3:1])([CH3:38])[CH3:39])([CH3:37])[C:14]4[C:9]([C:8]=3[OH:15])=[CH:10][CH:11]=[CH:12][CH:13]=4)=[N:17][S:18](=[O:35])(=[O:34])[C:19]=2[CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136384759HCID 136384759, compound

Product 1

HCID 136384756HCID 136384756, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 42E (1.91 g, 3.45 mmol) in 4 M hydrochloric acid in 1,4-dioxane (30 mL) was stirred at 25° C. for 1 hour. The solution was concentrated in vacuo and the residue was triturated in diethyl ether to give 1.58 g (93%) of a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 0.38 (td, J=12.87, 3.68 Hz, 1H) 0.78 (m, 10H) 1.59 (s, 3H) 2.08 (m, 1H) 2.23 (td, J=12.78, 4.60 Hz, 1H) 7.07 (m, 2H) 7.53 (m, 2H) 7.77 (m, 2H) 8.16 (d, J=7.72 Hz, 1H) 13.58 (s, 1H); MS (ESI+) m/z 454 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-77184342467949d8ad8fc7e6aaf6839c
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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