HCID 86701307, compound → HCID 86701306, compound

HRID 2283006Notes

Reaction equation

HRID 2283006 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][O:18][CH2:19][C@H:20]([O:29][CH2:30][C:31]([CH3:33])=[CH2:32])[C@@H:21]([O:24][CH2:25][C:26]([CH3:28])=[CH2:27])[CH2:22][OH:23])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.CS(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][O:18][CH2:19][C@H:20]([O:29][CH2:30][C:31]([CH3:33])=[CH2:32])[C@@H:21]([O:24][CH2:25][C:26]([CH3:28])=[CH2:27])[CH:22]=[O:23])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86701307HCID 86701307, compound

Product 1

HCID 86701306HCID 86701306, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Procedure

To a solution of (S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((2S,3S)-4-hydroxy-2,3-bis((2-methylallyl)oxy)butoxy)propanoate (3.96 g, 8.51 mmol) in CH2Cl2/DMSO (56.7 mL, ratio: 5/1) at 0° C. was added TEA (5.93 ml, 42.5 mmol) followed by sulfur trioxide pyridine complex (4.06 g, 25.5 mmol) and the reaction was slowly warmed to room temperature and stirred for 2 h. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were washed with H2O and brine, dried over MgSO4, filtered, and the filtrate was concentrated. The crude residue was purified by flash chromatography (SiO2, hexanes/EtOAc gradient) to provide the title compound as a colorless oil (3.26 g, 83% yield): IR (neat) 3360, 2951, 1721, 1512, 1209, 1053 cm−1; 1H NMR (400 MHz, CDCl3) δ 9.69 (d, J=1.0 Hz, 1H), 7.41-7.27 (m, 5H), 5.65 (d, J=8.7 Hz, 1H), 5.17-5.08 (m, 2H), 4.96-4.92 (m, 2H), 4.90 (d, J=14.8 Hz, 2H), 4.47 (dt, J=8.7, 2.9 Hz, 1H), 4.10 (d, J=12.4 Hz, 1H), 3.97-3.88 (m, 4H), 3.85-3.78 (m, 2H), 3.75 (s, 3H), 3.65 (dd, J=9.5, 3.2 Hz, 1H), 3.62 (d, J=4.5 Hz, 2H), 1.74 (s, 3H), 1.69 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 202.61, 170.65, 156.16, 141.73, 141.27, 136.42, 128.63, 128.26, 128.17, 113.83, 113.23, 82.49, 78.16, 75.45, 75.01, 71.55, 69.39, 67.16, 54.49, 52.70, 19.62, 19.55; ESIMS m/z 486.2 ([M+Na]+).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic phases were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude residue was purified by flash chromatography (SiO2, hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-58ae1b01fc2d4598890be1c5233ab7d2
Source dataset
uspto-grants-2015_09
Patent number
US09144239B2

Reaction notes

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