Nitrogen → HCID 86589057, compound

HRID 2414393Notes

Reaction equation

HRID 2414393 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH:18][C:19](=[O:40])[C@H:20]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[NH:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[CH2:27][O:26][C:25]3=[O:31])[C:16]#[N:17])[CH:8]=[CH:9][CH:10]=1)=[O:4].N#N>CC(=O)C(C)(C)C.CCOC(C)=O>[C:3]([C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH:18][C:19](=[O:40])[C@H:20]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[NH:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[CH2:27][O:26][C:25]3=[O:31])[C:16]#[N:17])[CH:8]=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 947NitrogenHCID 86589058HCID 86589058, compound

Product 1

HCID 86589057HCID 86589057, compound

Reagents, catalysts & solvents 2

HCID 6416PinacoloneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-(5-(3-methoxycarbonylphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(3-oxo-1,3-dihydro-isobenzofuran-5-yl)-L-phenylalaninamide (0.354 g, 0.67 mmol) in pinacolone (15 mL) is deoxygenated with bubbling N2 for 5 min., after which time Lil (0.90 g, 6.74 mmol) is added in one portion. The solution is then heated to 100° C. for 28 h. After cooling, it is diluted with EtOAc (100 mL), and washed with 1 N HCl (100 mL), and brine (50 mL), then dried (MgSO4), evaporated and chromatographed (2% MeOH/CH2Cl2, 0% to 0.05% acetic acid) to yield N-(5-(3-carboxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(3-oxo-1,3-dihydro-isobenzofuran-5-yl)-L-phenylalaninamide, as a light yellow solid; m.p. 91-94° C.

Workup

  1. additionafter which time Lil (0.90 g, 6.74 mmol) is added in one portion
  2. temperatureAfter cooling
  3. washwashed with 1 N HCl (100 mL), and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customchromatographed (2% MeOH/CH2Cl2, 0% to 0.05% acetic acid)

Sources & evidence

ORD record
ord-56574a174d904f6aa33a6e4cc1522f10
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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