Hydrochloric Acid → HCID 70657544, compound

HRID 1504158Notes

Reaction equation

HRID 1504158 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([CH2:19][N:20]([CH2:28][C:29]3[C:30]([CH2:35][OH:36])=[N:31][CH:32]=[CH:33][CH:34]=3)C(=O)OC(C)(C)C)[CH:17]=[CH:18][C:4]1=2)[CH3:2].Cl>C(O)C>[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([CH2:19][NH:20][CH2:28][C:29]3[C:30]([CH2:35][OH:36])=[N:31][CH:32]=[CH:33][CH:34]=3)[CH:17]=[CH:18][C:4]1=2)[CH3:2]

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-284a1d833cc444c4872134f6c44b1bd8
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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