Hydrochloric Acid → [8-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]acetic acid

HRID 1514268Notes

Reaction equation

HRID 1514268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:35]=[CH:34][C:20]4[CH2:21][N:22]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[CH2:23][CH2:24][O:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:35]=[CH:34][C:20]4[CH2:21][N:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:23][CH2:24][O:25][C:19]=4[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594035271,1-Dimethylethyl [8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]acetate

Product 1

HCID 44128824[8-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]acetic acidYield 38.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Dimethylethyl [8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]acetate (Preparation 37) (0.13 g, 0.260 mmol) was dissolved in 1,4-dioxane (1 ml) and 4M HCl (4 ml, 16.00 mmol) in dioxan was added and the reaction mixture was left at room temperature for 24 hours. Then the reaction mixture was evaporated, triturated with ether and the resulting solid filtered off. The solid was dissolved in 5 ml of 2M sodium hydroxide and acidified with acetic acid when solid separated. Attempted to dissolve in EtOAc but insoluble so filtered off and washed well with water, acetone and ether to give the title compound (44 mgs) as a white solid. δH (400 MHz, d6DMSO) 1.36 (6H, d), 3.13 (2H, br. s), 3.96 (2H, s), 4.08 (2H, br. s), 4.89 (1H, m), 7.38 (1H, d), 7.44 (1H, d), 7.61 (1H, s), 7.72 (1H, d), 8.11 (1H, d), 8.18 (1H, d), (remaining 2H signal obscured by solvent peak); MS (ES) C22H2235ClN3O5 requires 443; found 444 [M+H]+.

Workup

  1. customThen the reaction mixture was evaporated
  2. customtriturated with ether
  3. filtrationthe resulting solid filtered off
  4. dissolutionThe solid was dissolved in 5 ml of 2M sodium hydroxide
  5. customseparated
  6. dissolutionto dissolve in EtOAc
  7. filtrationinsoluble so filtered off
  8. washwashed well with water, acetone and ether

Sources & evidence

ORD record
ord-55106a20244c42eca02cb7ee562e31bb
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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