Hydrochloric Acid → HCID 136384654, compound

HRID 2224900Notes

Reaction equation

HRID 2224900 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:18])([CH2:12][CH2:13][C@@H:14]([CH3:17])[CH2:15][CH3:16])[C:4](=[O:19])[C:3]=1[C:20]1[NH:25][C:24]2[CH:26]=[CH:27][C:28]([NH:30]C(=O)OC(C)(C)C)=[CH:29][C:23]=2[S:22](=[O:39])(=[O:38])[N:21]=1.[ClH:40]>O1CCOCC1>[ClH:40].[NH2:30][C:28]1[CH:27]=[CH:26][C:24]2[NH:25][C:20]([C:3]3[C:4](=[O:19])[C:5]([CH3:18])([CH2:12][CH2:13][C@@H:14]([CH3:17])[CH2:15][CH3:16])[C:6]4[C:11]([C:2]=3[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=4)=[N:21][S:22](=[O:39])(=[O:38])[C:23]=2[CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136337511HCID 136337511, compound

Product 1

HCID 136384654HCID 136384654, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 43E (152 mg, 0.270 mmol) in 4 M hydrochloric acid in 1,4-dioxane (3 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 119 mg (88%) of a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 0.45 m, 1 H) 0.66 m, 6 H) 0.92 m, 2 H) 1.12 (m, 2H) 1.57 (s, 3 H) 2.15 m, 2 H) 7.01 m, 2 H) 7.46 (d, J=8.82 Hz, 1 H) 7.54 m, 1 H) 7.77 m, 2 H) 8.16 m, 1 H) 13.57 (s, 1 H); 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-4dc38d53c32a4165b07ea9b79843665f
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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