4-((((Benzyloxy)carbonyl)amino)methyl)benzoic acid → HCID 86592268, compound

HRID 11863

Reaction equation

HRID 11863 reaction equation
C([NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])(OC(C)(C)C)=O.CCN=C=NCCCN(C)C.[ClH:28].[C:29]([NH:39][CH2:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([OH:47])=O)=[CH:43][CH:42]=1)([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>CN(C=O)C.CN(C1C=CN=CC=1)C>[ClH:28].[C:29]([NH:39][CH2:40][C:41]1[CH:42]=[CH:43][C:44]([C:45]([NH:13][C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][CH2:10][CH2:9][NH2:8])=[O:47])=[CH:48][CH:49]=1)([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30]

Participants

7

Reactant 3

HCID 14799974-((((Benzyloxy)carbonyl)amino)methyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6993436(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acid

Product 2

HCID 313Hydrochloric AcidHCID 86592268HCID 86592268, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The compound obtained in Example 23-2 (350 mg) was dissolved in DMF (7 ml). After the addition of WSCI hydrochloride (265.0 g), DMAP (169 mg), and the compound obtained in Example 41-1 (276.0 mg), the mixture was stirred for 24 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform, washed with 1 mol/l aqueous solution of hydrochloric acid and saturated aqueous solution of sodium hydrogencarbonate, and dried over sodium hydrogensulfate. The solvent was removed by distillation and the residue was purified by silica gel column chromatography (20 g, chloroform/methanol=10/1). 130 mg of the obtained product was dissolved in methanol (2.6 ml) and 4 mol/l hydrochloric acid/dioxane solution (2.6 ml) was added. The mixture was stirred for 70 minutes at room temperature. After the reaction, the solvent was removed by distillation and the residue was dried under vacuum to obtain hydrochloride of the title compound (147 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l aqueous solution of hydrochloric acid and saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialdried over sodium hydrogensulfate
  6. customThe solvent was removed by distillation
  7. customthe residue was purified by silica gel column chromatography (20 g, chloroform/methanol=10/1)
  8. dissolution130 mg of the obtained product was dissolved in methanol (2.6 ml)
  9. addition4 mol/l hydrochloric acid/dioxane solution (2.6 ml) was added
  10. customAfter the reaction
  11. customthe solvent was removed by distillation
  12. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-447f2211d39544d9a51ee1929e302857
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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