Diphenyl N-Cyanocarbonimidate → HCID 178431175, compound

HRID 847169Notes

Reaction equation

HRID 847169 reaction equation
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].[CH:17]1[CH:22]=[CH:21][C:20]([O:23][C:24](OC2C=CC=CC=2)=[N:25][C:26]#[N:27])=[CH:19][CH:18]=1>C(O)(C)C>[C:26]([N:25]=[C:24]([NH:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:14])([CH3:15])[C@H:3]1[OH:16])[O:23][C:20]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1)#[N:27]

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 178431175HCID 178431175, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (prepared according to Evans et al., J. Med. Chem., 1983, 26, 1582 and J. Med. Chem., 1986, 29, 2194) (5.0 g, 23 mmol) in isopropanol (50 mL), diphenylcyanocarbonimidate (5.5 g, 25 mmol) was added at room temperature and the reaction mixture was allowed to stir at room temperature for 16 hours. Most of the isopropanol was evaporated and the residue was dissolved in ethyl acetate. The resulting solution was washed successively with 10% citric acid, 1N sodium hydroxide solution and brine. It was dried over anhydrous magnesium sulfate, concentrated and the residue was crystallized from chloroform-isopropyl ether to yield the title A compound (4.2 g) as a colorless solid, m.p. 186°-188° C.

Workup

  1. customMost of the isopropanol was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe resulting solution was washed successively with 10% citric acid, 1N sodium hydroxide solution and brine
  4. dry with materialIt was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue was crystallized from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-e52d0078fc6f41b8845be368280b8ac4
Source dataset
uspto-grants-1992_08
Patent number
US05140031

Reaction notes

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