Water → HCID 86758642, compound

HRID 2298045Notes

Reaction equation

HRID 2298045 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1Cl)([OH:3])=O.[C:25]12([CH2:35][NH2:36])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.O.[CH3:38]N(C)C=O>>[CH3:38][C:9]1[CH:8]=[CH:7][C:6]([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]2)=[CH:5][C:4]=1[C:1]([NH:36][CH2:35][C:25]12[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2)=[O:3]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 86758643HCID 86758643, compound

Product 1

HCID 86758642HCID 86758642, compound

Procedure

A solution of 4-(3-carboxy-4-chlorophenyl)hexahydro-1H-1,4-diazepine-1-carboxylic acid, 1,1-dimethylethyl ester (Example 5b, 0.10 g) and N,N′-carbonyldiimidazole (0.045 g) in dimethylformamide (3 ml) was stirred at room temperature for 2 h. 1-Adamantanemethylamine (0.050 ml) was then added and stirring continued for 14 h. The reaction mixture was poured into water and extracted with ethyl acetate three times. The ethyl acetate layers were combined and washed with 2M hydrochloric acid, 10% aqueous sodium hydroxide and brine, then dried over magnesium sulfate and concentrated under reduced pressure. Purification by chromatography on silica gel, eluting with 20-30% ethyl acetate in iso-hexane, gave the subtitle product as a gum which crystallised on standing.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washwashed with 2M hydrochloric acid, 10% aqueous sodium hydroxide and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography on silica gel
  6. washeluting with 20-30% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-b5467f87cc434b93b5c01e3ab6db3403
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

Loading…