Water → HCID 58204798, compound

HRID 886092Notes

Reaction equation

HRID 886092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[N:14]=[C:15]2[C:21]3[CH:22]=[C:23]([C:26]([O:28]C)=[O:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][CH2:17][N:16]2[CH:30]=1.O1CCCC1.O.O.[OH-].[Li+]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[N:14]=[C:15]2[C:21]3[CH:22]=[C:23]([C:26]([OH:28])=[O:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][CH2:17][N:16]2[CH:30]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 58204585methyl 2-(1-(2-chlorophenyl)-1H-imidazol-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate

Product 1

HCID 58204798HCID 58204798, compound

Procedure

To a solution of methyl 2-(1-(2-chlorophenyl)-1H-imidazol-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate (0.100 g, 0.238 mmol) in tetrahydrofuran (5.56 mL, 68.5 mmol) and Water (5.56 mL, 308 mmol) was added Lithium hydroxide, monohydrate (0.0399 g, 0.950 mmol). The reaction mixture was stirred at rt o/n. The reaction mixture was concentrated. The reaction mixture was acidified with 1M HCl then extracted with DCM (3×). The combined organics were dried over Na2SO4, filtered and concentrated to give 2-(1-(2-chlorophenyl)-1H-imidazol-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylic acid. MS: (ESI+)=407.2

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthen extracted with DCM (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd57901b860042f28e900d08dab2ac2b
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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