Dichloromethane → HCID 59704211, compound

HRID 2427483Notes

Reaction equation

HRID 2427483 reaction equation
C1C2C(OC(=O)[N:16](C)[CH2:17][C:18](=[O:45])[NH:19][C:20]3[C:29]([NH2:30])=[C:28]4[C:23]([C@@H:24]([C:34]5[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([Br:44])[CH:35]=5)[C:25]([C:32]#[N:33])=[C:26]([NH2:31])[O:27]4)=[CH:22][CH:21]=3)C3C(=CC=CC=3)C=2C=CC=1.C(Cl)Cl.[OH-].[Na+]>CO>[NH2:16][CH2:17][C:18]([NH:19][C:20]1[C:29]([NH2:30])=[C:28]2[C:23]([C@@H:24]([C:34]3[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([Br:44])[CH:35]=3)[C:25]([C:32]#[N:33])=[C:26]([NH2:31])[O:27]2)=[CH:22][CH:21]=1)=[O:45]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 86619503HCID 86619503, compound

Product 1

HCID 59704211HCID 59704211, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an oven-dried one-neck round bottom reaction flask charged with a magnetic stir bar at rt under argon was added (9H-fluoren-9-yl)methyl((R)-2,8-diamino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-4H-chromen-7-ylcarbamoyl)methylcarbamate (0.050 g, 0.072 mmol), CH2Cl2:MeOH, 1:1 (2.40 mL) and 2N NaOH (0.072 mL, 0.14 mmol). The orange suspension was stirred at rt overnight. The suspension was concentrated leaving a brown residue. The residue was extracted with CHCl3 (3×40 mL), dried over MgSO4, filtered and concentrated to give the crude product. Purification by flash column chromatography (silica gel 4 g pre-packed column, gradient elution with CH2Cl2:MeOH, 96:4 to 90:10 with trace Et3N) gave 0.012 g (35%) of the title compound as a yellow solid: 1H-NMR (CDCl3): 9.34 (br s, 1H), 6.90 (d, J=1.9 Hz, 1H), 6.89 (d, J=8.5 Hz, 1H), 6.71 (d, J=1.9 Hz, 1H), 6.37 (d, J=8.2 Hz, 1H), 4.72 (br s, 2H), 4.64 (s, 1H), 4.29 (br s, 2H), 3.84 (s, 3H), 3.83 (s, 3H), 3.54 (br s, 2H).

Workup

  1. additionTo an oven-dried one-neck round bottom reaction flask charged with a magnetic stir bar at rt under argon
  2. concentrationThe suspension was concentrated
  3. customleaving a brown residue
  4. extractionThe residue was extracted with CHCl3 (3×40 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product
  9. customPurification
  10. washby flash column chromatography (silica gel 4 g pre-packed column, gradient elution with CH2Cl2:MeOH, 96:4 to 90:10 with trace Et3N)

Sources & evidence

ORD record
ord-c395f08666b74883b7094187dae29043
Source dataset
uspto-grants-2011_06
Patent number
US07968595B2

Reaction notes

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