Hydrochloric Acid → HCID 70657544, compound

HRID 68986Notes

Reaction equation

HRID 68986 reaction equation
C(OC(=O)[N:7]([CH2:17][C:18]1[CH:35]=[CH:34][C:21]2[N:22]([CH2:32][CH3:33])[C:23](=[O:31])[C:24]([CH3:30])([CH3:29])[C:25](=[O:28])[N:26]([CH3:27])[C:20]=2[CH:19]=1)[CH2:8][C:9]1[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C.Cl>C(O)C>[CH2:32]([N:22]1[C:23](=[O:31])[C:24]([CH3:30])([CH3:29])[C:25](=[O:28])[N:26]([CH3:27])[C:20]2[CH:19]=[C:18]([CH2:17][NH:7][CH2:8][C:9]3[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=3)[CH:35]=[CH:34][C:21]1=2)[CH3:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66959969HCID 66959969, compound

Product 1

HCID 70657544HCID 70657544, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a ethanol solution (20 ml) of tert-butyl(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl)methyl((2-(hydroxymethyl)pyridin-3-yl)methyl)carbamate (0.82 g) was added 5 M HCl and the mixture was stirred at 50° C. for 7 hours. The resulting mixture was concentrated and then 5 M NaOH was added thereto. Organic materials were extracted with ethyl acetate twice and then dried over MgSO4. After evaporation, the residue was purified by column chromatography (methanol/ethyl acetate 1:9→1:1) to give the titled compound as pale yellow oil (0.37 g).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. addition5 M NaOH was added
  3. extractionOrganic materials were extracted with ethyl acetate twice
  4. dry with materialdried over MgSO4
  5. customAfter evaporation
  6. customthe residue was purified by column chromatography (methanol/ethyl acetate 1:9→1:1)

Sources & evidence

ORD record
ord-b94c1465ff574f899634694fc608530f
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…