Hydrochloric Acid → HCID 68638699, compound

HRID 1253884Notes

Reaction equation

HRID 1253884 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][N:8]([C:16](=[O:37])[CH2:17][CH:18]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=2[F:28])[CH2:7][C:6]1=[O:38].[OH-].[Li+].Cl>C1COCC1.O>[C:33]([O:32][C:30]([NH:29][CH:18]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:17][C:16]([N:8]1[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:5]([CH2:4][C:3]([OH:39])=[O:2])[C:6](=[O:38])[CH2:7]1)=[O:37])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68638028HCID 68638028, compound

Product 1

HCID 68638699HCID 68638699, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {4-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-2-oxo-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl}-acetic acid methyl ester (90 mg, 0.16 mmol) in THF (2 mL) and water (2 mL), was added lithium hydroxide (40 mg, 0.95 mmol). The reaction mixture was stirred at r.t. overnight. After the completion of the reaction as confirmed by TLC, the reaction mixture was cooled to 0° C. and neutralized with 10% HCl solution and the pH was adjusted to 1. The crude compound was extracted with ethylacetate (10 mL). The organic layer was washed with water, dried over Na2SO4. The solvents were removed in vacuo to afford {4-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-2-oxo-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl}-acetic acid (70 mg, 82%) as a viscous oil.

Workup

  1. customAfter the completion of the reaction
  2. extractionThe crude compound was extracted with ethylacetate (10 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-933a5a2855414b9cbbe975639745e717
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

Loading…