Hydrochloric Acid → HCID 24768947, compound

HRID 502533Notes

Reaction equation

HRID 502533 reaction equation
C([O:5][P:6]([O:40]C(C)(C)C)([O:8][CH2:9][O:10][C:11](=[O:39])[N:12]([C:36](=[O:38])[CH3:37])[CH2:13][C@@H:14]1[O:18][C:17](=[O:19])[N:16]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:33][C:32]4[C:28](=[N:29][N:30]([CH3:34])[CH:31]=4)[CH2:27]3)=[C:22]([F:35])[CH:21]=2)[CH2:15]1)=[O:7])(C)(C)C.Cl.C(OCC)C>ClCCl>[P:6]([O:8][CH2:9][O:10][C:11](=[O:39])[N:12]([C:36](=[O:38])[CH3:37])[CH2:13][C@@H:14]1[O:18][C:17](=[O:19])[N:16]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:33][C:32]4[C:28](=[N:29][N:30]([CH3:34])[CH:31]=4)[CH2:27]3)=[C:22]([F:35])[CH:21]=2)[CH2:15]1)([OH:7])([OH:40])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68468814HCID 68468814, compound

Product 1

HCID 24768947HCID 24768947, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17a (500 mg, 0.78 mmol) in dichloromethane (2.5 mL) under an atmosphere of nitrogen was added a solution of 1N HCl in diethyl ether (2.34 mL, 2.34 mmol) and the reaction mixture was stirred at rt for 3 h. The reaction mixture was concentrated in vacuo, purified directly by HPLC (C-18 column, 10-100% gradient elution, MeCN:H2O), and fractions containing product were lyophilized to give 290 mg (70%) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 7.53 (s, 1H), 7.42 (dd, 1H), 7.16 (dd, 1H), 6.87 (dd, 1H), 5.65 (dd, 1H), 5.58 (dd, 1H), 4.87-4.80 (m, 1H), 4.48-4.46 (m, 4H), 4.20 (dd, 1H), 4.09 (dd, 1H), 3.87 (dd, 1H), 3.84 (s, 3H), 3.78 (dd, 1H), and 2.49 (s, 3H). MS 528 (M+1)+

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified directly by HPLC (C-18 column, 10-100% gradient elution, MeCN:H2O), and fractions
  3. additioncontaining product

Sources & evidence

ORD record
ord-1d7d5d89ce5843c29da83b210c351179
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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