Hydrochloric Acid → HCID 24769049, compound

HRID 502539Notes

Reaction equation

HRID 502539 reaction equation
[C:1]([N:4]([CH2:26][C@@H:27]1[O:31][C:30](=[O:32])[N:29]([C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH2:46][C:45]4[C:41](=[N:42][N:43]([CH3:47])[CH:44]=4)[CH2:40]3)=[C:35]([F:48])[CH:34]=2)[CH2:28]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:25])[CH2:11][O:12][P:13]([O:20]C(C)(C)C)([O:15]C(C)(C)C)=[O:14])=[O:6])(=[O:3])[CH3:2].Cl.C(OCC)C>ClCCl>[C:1]([N:4]([CH2:26][C@@H:27]1[O:31][C:30](=[O:32])[N:29]([C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH2:46][C:45]4[C:41](=[N:42][N:43]([CH3:47])[CH:44]=4)[CH2:40]3)=[C:35]([F:48])[CH:34]=2)[CH2:28]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:25])[CH2:11][O:12][P:13]([OH:20])([OH:15])=[O:14])=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86618075HCID 86618075, compound

Product 1

HCID 24769049HCID 24769049, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 23 (20 mg, 0.03 mmol) in dichloromethane (1 mL) under nitrogen was added dropwise a solution of 1N HCl in diethyl ether (2.0 mL, 2.0 mmol). The reaction mixture was stirred for 1 h at rt, concentrated in vacuo, and purified directly by HPLC (C-18 column, 10-70% gradient elution, MeCN:H2O with 0.1% TFA) to give 5 mg (25%) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 7.53 (s, 1H), 7.42 (dd, 1H), 7.15 (dd, 1H), 6.87 (dd, 1H), 5.88 (s, 2H), 4.79-4.72 (m, 1H), 4.53 (d, 2H), 4.48-4.46 (m, 4H), 4.15-4.07 (m, 2H), 3.88 (dd, 1H), 3.85 (s, 3H), 3.76 (dd, 1H), and 2.46 (s, 3H). MS 586 (M+1)+

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified directly by HPLC (C-18 column, 10-70% gradient elution, MeCN:H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-b384a151d1114669a730bf2bf41a117a
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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