Lithium Hydroxide → HCID 68793468, compound

HRID 899927Notes

Reaction equation

HRID 899927 reaction equation
[OH-].[Li+].[CH3:3][CH:4]([CH3:46])[CH2:5][CH2:6][N:7]([CH2:41][CH2:42][CH:43]([CH3:45])[CH3:44])[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([NH:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[N:15]([CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:14]=2[CH:40]=1)=[O:9]>O1CCCC1.O.C(OCC)C>[CH3:44][CH:43]([CH3:45])[CH2:42][CH2:41][N:7]([CH2:6][CH2:5][CH:4]([CH3:46])[CH3:3])[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([NH:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)[N:15]([CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[C:14]=2[CH:40]=1)=[O:9]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68792031methyl 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl) amino]propyl}-1H-benzimidazol-2-yl)amino]benzoate

Product 1

HCID 68793468HCID 68793468, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (141 mg, 5 eq) is added to methyl 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl)amino]propyl}-1H-benzimidazol-2-yl)amino]benzoate prepared according to reaction diagram A, Example A1, (405 mg, 1 eq) in a mixture of tetrahydrofuran (4 ml) and water (3 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. Dichloromethane (50 ml) and water (20′ ml) are added to the residue. The mixture is acidified by the addition of acetic acid to pH 5. After decantation and extractions, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The solid obtained is taken up in ethyl ether in order to produce the expected compound (309 mg; 79%).

Workup

  1. customprepared
  2. customaccording to reaction diagram A, Example A1, (405 mg, 1 eq)
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for 18 hours
  5. concentrationconcentrated under reduced pressure at 40° C
  6. additionDichloromethane (50 ml) and water (20′ ml) are added to the residue
  7. additionThe mixture is acidified by the addition of acetic acid to pH 5
  8. extractionAfter decantation and extractions
  9. dry with materialthe combined organic phases are dried over sodium sulphate
  10. concentrationconcentrated under reduced pressure
  11. customThe solid obtained

Sources & evidence

ORD record
ord-a0557b498200486a8367de7dc841fb8f
Source dataset
uspto-grants-2008_04
Patent number
US07355052B2

Reaction notes

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