Hydrochloric Acid → HCID 86658579, compound

HRID 1400884Notes

Reaction equation

HRID 1400884 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[N:25]=[CH:26][N:27]([CH2:29][CH:30](OCC)[O:31]CC)[CH:28]=5)[S:23][C:16]=34)=[C:10]([F:37])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1.Cl>CC(O)=O.O>[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[N:25]=[CH:26][N:27]([CH2:29][CH:30]=[O:31])[CH:28]=5)[S:23][C:16]=34)=[C:10]([F:37])[CH:9]=2)=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67441318HCID 67441318, compound

Product 1

HCID 86658579HCID 86658579, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of acetal 263 (2.95 g, 5.61 mmol) in AcOH/H2O (20/20 mL) was added concentrated HCl (2 mL) and the reaction mixture was heated at 90° C. for 1 h. The reaction mixture was concentrated, diluted with water and 4M NaOH to pH 10 to form a precipitate that was collected by filtration, washed with water and dried under vacuum. The material was then purified by Biotage (SNAP 100 g cartridge; 2% of ammonium hydroxide in MeOH/DCM: 0/100 to 15/85, over 20 CV) to afford the title compound 264 (1.2 g, 2.66 mmol, 47% yield) as a brown solid. MS (m/z): 484.51 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water and 4M NaOH to pH 10
  3. customto form a precipitate that
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried under vacuum
  7. customThe material was then purified by Biotage (SNAP 100 g cartridge; 2% of ammonium hydroxide in MeOH/DCM: 0/100 to 15/85, over 20 CV)

Sources & evidence

ORD record
ord-a7b47ea08c644d549dbeb7307edf184a
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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