Diisopropylethylamine → HCID 178462635, compound

HRID 20167

Reaction equation

HRID 20167 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=2[F:16])[CH2:5][N:4]([CH2:17][CH3:18])[C:3]1=[O:19].C(N(CC)C(C)C)(C)C.[CH:29]1[CH:34]=[CH:33][C:32]([O:35][C:36](OC2C=CC=CC=2)=[N:37][C:38]#[N:39])=[CH:31][CH:30]=1>ClCCl>[C:38]([N:37]=[C:36]([O:35][C:32]1[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=1)[NH:1][C@@H:2]1[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=2[F:16])[CH2:5][N:4]([CH2:17][CH3:18])[C:3]1=[O:19])#[N:39]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 66939267(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-ethylazepan-2-one

Product 1

HCID 178462635HCID 178462635, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-ethylazepan-2-one (135 mg, 0.503 mmol) in dichloromethane was treated N,N-diisopropylethylamine (65 mg, 0.503 mmol) and diphenyl N-cyanocarbonimidate (204 mg, 0.855 mmol). After 5 h, the reaction was quenched with 0.5N NaOH and the organic layer washed with water and brine. The combined aqueous layers were extracted with EtOAc. The combined organics were dried, filtered and concentrated. Purification by silica gel chromatography (EtOAc/hexanes) gave the title compound (166 mg). MS 413.3 (M+1).

Workup

  1. customthe reaction was quenched with 0.5N NaOH
  2. washthe organic layer washed with water and brine
  3. extractionThe combined aqueous layers were extracted with EtOAc
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-95e9b61a3fd14b9a8b4ba1cd207bfeac
Source dataset
uspto-grants-2010_06
Patent number
US07745427B2

Linked notes

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