Dimethylformamide → HCID 21193267, compound

HRID 1068459Notes

Reaction equation

HRID 1068459 reaction equation
C(OC([N:8]1[CH2:16][CH2:15][C:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)([C:12](O)=[O:13])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CN(C)[CH2:28][CH2:29][CH2:30]N=C=NCC.[OH2:37].ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+:49].[CH:50](N(C(C)C)CC)(C)C.CN(C)[CH:61]=[O:62]>>[C:29]([O:37][C:61]([NH:49][C:12](=[O:13])[C:11]1([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)[CH2:15][CH2:16][NH:8][CH2:9][CH2:10]1)=[O:62])([CH3:30])([CH3:50])[CH3:28]

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21193367HCID 21193367, compound

Product 1

HCID 21193267HCID 21193267, compound

Procedure

A mixture of N-tert-butoxycarbonyl-4-(3-methylbenzyl)-isonipecotic acid (1.02 g, 3.00 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.64 g. 3.36 mmol), 1-hydroxy-benzotriazole hydrate (0.45 g, 3.31 mmol), ammonium chloride (0.33 g, 6.15 mmol), and diisopropylethylamine (1.15 mL, 6.60 mmol) in anhydrous dimethylformamide (10 ml) was stirred at room temp. overnight. The resultant solution was concentrated under vacuum and the residue was partitioned between ethyl acetate and water. The organic extracts were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residual oil was subjected to column chromatography on silica eluting with 40% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title product.

Workup

  1. concentrationThe resultant solution was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-a352930e26614ea9ba4ac728620a1cec
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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