Phosphate → HCID 69077824, compound

HRID 747066Notes

Reaction equation

HRID 747066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH:12]2[CH2:18][C:19]([NH:21][C@@H:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([CH:32]=O)[CH:28]=3)[CH2:23]2)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:34](O)(C)(C)C.C1COCC1.O.C[N+]1([O-])CCOCC1.P([O-])([O-])([O-])=O>CCOC(C)=O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH:12]2[CH2:18][C:19]([NH:21][C@@H:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([CH:32]=[CH2:34])[CH:28]=3)[CH2:23]2)=[O:20])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1061PhosphateHCID 82029Methyl morpholine oxideHCID 22124471t-Butanol tetrahydrofuran waterHCID 86628164HCID 86628164, compound

Product 1

HCID 69077824HCID 69077824, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(1-(4-chlorophenylsulfonyl)-3-oxopiperazin-2-yl)acetic acid (332 mg, 1 mmol), crude 48999-36 (190 mg, 1.1 mmol), II (135 mg, 1 mmol) and III (191 mg, 1 mmol) in 1 mL of DMF was stirred overnight at room temperature. After quenching with sat. NaHCO3 solution, the reaction mixture was extracted with EtOAc. The combined organic phase was washed brine, dried over Na2SO4, and evaporated in vaco. Flash chromatography (SiO2, EtOAc to EtOAc/MeOH=100:3 to 100:5 to 100:6) gave the title compound as a white solid. E. Preparation of (R)-2-(1-(4-chlorophenylsulfonyl)-3-oxopiperazin-2-yl)-N-(6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide. To a solution of the procuct of step D. (280 mg, 0.575 mmol) in 13 mL of a mixture solvent t-butanol/THF/water (10:2:1) was added NMO (135 mg, 1.15 mmol), followed by OsO4 (2.5% w/w in t-butanol, 175 mg, 0.017 mmol). After stirring overnight at room temperature, 4 mL of pH 7.2 phosphate buffer was added, followed by NaIO4 (615 mg, 2.875 mmol). After stirring for 5 h at room temperature, the reaction solution was diluted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and evaporated to dryness in vaco. Flash chromatography (SiO2, EtOAc/hexane=1:1) afforded the title compound as a white solid. Preparation of (R)-2-(1-(4-chlorophenylsulfonyl)-3-oxopiperazin-2-yl)-N-(6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide.

Workup

  1. stirringAfter stirring for 5 h at room temperature
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated to dryness in vaco

Sources & evidence

ORD record
ord-bb43d06b44de409db3cf50b725c30ddd
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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