Triethylamine → HCID 11341141, compound

HRID 1725660Notes

Reaction equation

HRID 1725660 reaction equation
C(N(CC)CC)C.[NH2:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=2[F:23])[CH2:12][N:11]([CH2:24][CH2:25][O:26][CH3:27])[C:10]1=[O:28].Cl[C:30](OC1C=CC([N+]([O-])=O)=CC=1)=[O:31].[NH:42]1[CH2:47][CH2:46][CH:45]([N:48]2[CH2:52][C:51](=[O:53])[NH:50][C:49]2=[O:54])[CH2:44][CH2:43]1>O1CCCC1>[F:23][C:17]1[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:16]=1[C@H:13]1[CH2:12][N:11]([CH2:24][CH2:25][O:26][CH3:27])[C:10](=[O:28])[C@H:9]([NH:8][C:30]([N:42]2[CH2:43][CH2:44][CH:45]([N:48]3[CH2:52][C:51](=[O:53])[NH:50][C:49]3=[O:54])[CH2:46][CH2:47]2)=[O:31])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 574289231-Piperidin-4-ylimidazolidine-2,4-dioneHCID 60037873(3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-(2-methoxyethyl)azepan-2-one

Product 1

HCID 11341141HCID 11341141, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.012 mL, 0.084 mmol) was added to a solution (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2-methoxyethyl)azepan-2-one (25 mg, 0.084 mmol) and p-nitrophenyl chloroformate (25 mg, 0.126 mmol) in tetrahydrofuran (1 mL) at 0° C. After 0.5 h, triethylamine (0.036 mL, 0.252 mmol) and 1-piperidin-4-ylimidazolidine-2,4-dione (23 mg, 0.126 mmol) were added and the mixture was allowed to warm to ambient temperature. After 1 h, the mixture was quenched with water, extracted with ethyl acetate, and washed with 1 N NaOH solution. The combined organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (0.5% methanol/dichloromethane→7% methanol/dichloromethane) gave the title compound (9 mg). MS 508.2 (M+1).

Workup

  1. waitAfter 1 h
  2. customthe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washwashed with 1 N NaOH solution
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (0.5% methanol/dichloromethane→7% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7247361675a847babdbeae88b93a52af
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

Loading…