Hydrochloric Acid → HCID 57529644, compound

HRID 1015478Notes

Reaction equation

HRID 1015478 reaction equation
Cl.[O:2]=[C:3]1[N:9]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C@H:19]([CH2:41][C:42]3[CH:47]=[C:46]([Br:48])[CH:45]=[C:44]([Br:49])[CH:43]=3)[C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH:28]4[CH2:33][CH2:32][N:31](OC(C)(C)C)[C:30](=C=O)[CH2:29]4)[CH2:24][CH2:23]3)=[O:21])=[O:17])[CH2:12][CH2:11]2)[CH2:8][CH2:7][C:6]2[CH:50]=[CH:51][CH:52]=[CH:53][C:5]=2[NH:4]1.CCOC(C)=O.C([O-])([O-])=O.[Na+].[Na+]>O>[O:2]=[C:3]1[N:9]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C@H:19]([CH2:41][C:42]3[CH:47]=[C:46]([Br:48])[CH:45]=[C:44]([Br:49])[CH:43]=3)[C:20](=[O:21])[N:22]3[CH2:27][CH2:26][N:25]([CH:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)[CH2:24][CH2:23]3)=[O:17])[CH2:12][CH2:11]2)[CH2:8][CH2:7][C:6]2[CH:50]=[CH:51][CH:52]=[CH:53][C:5]=2[NH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 86608968HCID 86608968, compound

Product 1

HCID 57529644HCID 57529644, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.8 mL HCl (3.2 M) were added to a solution of 180 mg (0.21 mmol) of (R)-1-(3,5-dibromo-benzyl)-2-[4-(1-tert-butoxy-carbonyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 64) in 2 mL water and the reaction mixture was stirred for 3 h at RT. The mixture was combined with 25 mL EtOAc and 20 mL 17% Na2CO3 solution, the organic phase was separated off, the aqueous phase was extracted again with 25 mL EtOAc, the combined organic phases were washed with 10 mL saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was suspended in diethyl ether, the organic phase was decanted off and the residue was dried.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted again with 25 mL EtOAc
  3. washthe combined organic phases were washed with 10 mL saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customthe organic phase was decanted off
  6. customthe residue was dried

Sources & evidence

ORD record
ord-7d7e41194834454082c7b57cc25b997f
Source dataset
uspto-grants-2011_07
Patent number
US07985747B2

Reaction notes

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