Sodium Sulfite → HCID 68325608, compound

HRID 2403288Notes

Reaction equation

HRID 2403288 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[CH:25][C:24](SC)=[CH:23][N:22]=3)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:30]1C=C(C=CC=1)C(OO)=O.[O-:40][S:41]([O-:43])=O.[Na+].[Na+]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]([S:41]([CH3:30])(=[O:43])=[O:40])=[CH:25][N:26]=3)=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 68325617HCID 68325617, compound

Product 1

HCID 68325608HCID 68325608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-2-[4-(5-methylsulfanyl-pyrimidin-2-ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (72 mg) in dichloromethane (5 ml) was added 3-chloroperoxybenzoic acid (77.2 mg). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was then poured into saturated aq. Na2SO3 solution and extracted twice with dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford (S)-2-[4-(5-methanesulfonyl-pyrimidin-2-ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (84 mg, quant.) as a light brown foam which was used in the next step without further purification. MS (ISP): 435.2 ([M+H]+), 379.2 ([M+H—C4H8]+).

Workup

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94370e847e224477ac36d241ffa8d4c0
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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