Hydrochloric Acid → HCID 24768826, compound

HRID 502528Notes

Reaction equation

HRID 502528 reaction equation
[C:1]([N:4]([CH2:22][C@@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:42][C:41]4[C:37](=[N:38][N:39]([CH3:43])[CH:40]=4)[CH2:36]3)=[C:31]([F:44])[CH:30]=2)[CH2:24]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:21])[CH2:11][N:12](C(OC(C)(C)C)=O)[CH3:13])=[O:6])(=[O:3])[CH3:2].Cl.CCOCC>C(Cl)Cl>[C:1]([N:4]([CH2:22][C@@H:23]1[O:27][C:26](=[O:28])[N:25]([C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:42][C:41]4[C:37](=[N:38][N:39]([CH3:43])[CH:40]=4)[CH2:36]3)=[C:31]([F:44])[CH:30]=2)[CH2:24]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:21])[CH2:11][NH:12][CH3:13])=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 24768888HCID 24768888, compound

Product 1

HCID 24768826HCID 24768826, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9 (50 mg, 0.08 mmol) in CH2Cl2 (2 mL) under nitrogen was added 1N HCl in Et2O (2.0 mL, 2.0 mmol). The reaction mixture was stirred at rt for 2 h, concentrated in vacuo, and purified directly by HPLC (C-18 column, 30-80% gradient elution, MeCN:H2O with 0.1% TFA). Fractions containing product were lyophilized to give 15 mg (36%) of the title compound as the trifluoroacetate salt. 1H NMR (400 MHz, DMSO-d6): δ 9.07 (br s, 1H), 7.54 (s, 1H), 7.43 (dd, 1H), 7.16 (dd, 1H), 6.87 (dd, 1H), 5.96-5.92 (m, 2H), 4.80-4.74 (m, 1H), 4.48-4.46 (m, 4H), 4.15-4.09 (m, 4H), 3.91 (dd, 1H), 3.85 (s, 3H), 3.76 (dd, 1H), 2.62 (s, 3H), 2.47 (s, 3H). MS 519 (M+1)+

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified directly by HPLC (C-18 column, 30-80% gradient elution, MeCN:H2O with 0.1% TFA)
  3. additionFractions containing product

Sources & evidence

ORD record
ord-b568425f5746464faa92058922368516
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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