Water → HCID 67287632, compound

HRID 1045329Notes

Reaction equation

HRID 1045329 reaction equation
C(Br)(Br)(Br)Br.[P:6]([O:11]C)([O:9][CH3:10])[O:7][CH3:8].[C:13]([O:17][C:18]([NH:20][C@@:21]([CH3:45])([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]2[CH:38]=[C:37]([CH3:39])[CH:36]=[CH:35][C:34]=2[O:40][CH2:41][O:42][CH3:43])=[CH:28][C:27]=1[Cl:44])[CH2:22][OH:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].O>N1C=CC=CC=1>[C:13]([O:17][C:18]([NH:20][C@@:21]([CH3:45])([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]2[CH:38]=[C:37]([CH3:39])[CH:36]=[CH:35][C:34]=2[O:40][CH2:41][O:42][CH3:43])=[CH:28][C:27]=1[Cl:44])[CH2:22][O:23][P:6]([O:9][CH3:10])([O:7][CH3:8])=[O:11])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8472Trimethyl phosphiteHCID 11205Carbon tetrabromideHCID 67287172Carbamic acid, N-[(1S)-3-[2-chloro-4-[[2-(methoxymethoxy)-5-methylphenyl]thio]phenyl]-1-(hydroxymethyl)-1-methylpropyl]-, 1,1-dimethylethyl ester

Product 1

HCID 67287632HCID 67287632, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Carbon tetrabromide (130 mg) and trimethyl phosphite (46 μL) were added under ice cooling to a solution of the compound of Example 20 (97 mg) in pyridine (0.5 mL) to form a reaction solution. This reaction solution was stirred for 2 hours under ice cooling. Then, water was added to the reaction solution, and the reaction solution was extracted with ethyl acetate. The extract was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the target product (84 mg) as a colorless oil.

Workup

  1. customto form a reaction solution
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe anhydrous sodium sulfate was removed by filtration
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-990d0d155d49422eb6afeeba5b97211e
Source dataset
uspto-grants-2013_10
Patent number
US08569270B2

Reaction notes

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