Sodium ethanethiolate → HCID 68440407, compound

HRID 2246982Notes

Reaction equation

HRID 2246982 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@H:11]([CH2:42][C:43]([CH3:48])([CH3:47])[C:44]([OH:46])=[O:45])[CH2:10]2)=[CH:5][CH:4]=1.C([S-])C.[Na+]>CN(C)C=O.Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)(=[O:34])=[O:33])[C@H:11]([CH2:42][C:43]([CH3:48])([CH3:47])[C:44]([OH:46])=[O:45])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 68440062HCID 68440062, compound

Product 1

HCID 68440407HCID 68440407, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 1.1 g of 3-[(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-2,2-dimethyl-propionic acid (from example 65b) in 10 ml N,N-dimethylformamide are added 1.35 g of sodium ethanethiolate and the reaction mixture is heated to 95° C. for 2 days. The reaction mixture is diluted with 1N hydrochloric acid solution and extracted with tert-butyl methyl ether. The organic phases are combined, dried and concentrated under reduced pressure to afford the crude title compound. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a colourless oil. Rf=0.10 (EtOAc-heptane 1:1); Rt=4.67.

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude title compound
  5. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-cbc826fbab9b42028fdd343ae3a80988
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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