Potassium Carbonate → (S)-3-(2-Amino-7-isopropyl-4-methyl-benzothiazol-6-ylsulfanyl)-4-hydroxy-6-[2-(4-hydroxyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

HRID 23512Notes

Reaction equation

HRID 23512 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([CH:11]([CH3:13])[CH3:12])=[C:9]([S:14]S(C3C=CC(C)=CC=3)(=O)=O)[CH:8]=[C:7]([CH3:25])[C:5]=2[N:6]=1.[OH:26][C:27]1[CH2:32][C@@:31]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=2)([CH:33]([CH3:35])[CH3:34])[O:30][C:29](=[O:45])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]2[C:10]([CH:11]([CH3:12])[CH3:13])=[C:9]([S:14][C:28]3[C:29](=[O:45])[O:30][C@:31]([CH2:36][CH2:37][C:38]4[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=4)([CH:33]([CH3:35])[CH3:34])[CH2:32][C:27]=3[OH:26])[CH:8]=[C:7]([CH3:25])[C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 54682331(S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-oneHCID 86592610toluene-4-thiosulfonic acid S-(2-amino-7-isopropyl-4-methyl-benzothiazol-6-yl)ester

Product 1

HCID 54689397(S)-3-(2-Amino-7-isopropyl-4-methyl-benzothiazol-6-ylsulfanyl)-4-hydroxy-6-[2-(4-hydroxyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to General Method 16a using toluene-4-thiosulfonic acid S-(2-amino-7-isopropyl-4-methyl-benzothiazol-6-yl)ester (Example BB-5; 0.35 g, 1.27 mmol), (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (Example J-10; 0.35 g. 1.27 mmol), potassium carbonate (0.7 g), and DMF (5 mL). The crude reaction mixture was purified by flash chromatography (20% EtOAc in hexanes to 50% EtOAc in hexanes to 5% MeOH in EtOAc as eluents), mp 232-234° C. MS (APCI): 513 (M+H).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash chromatography (20% EtOAc in hexanes to 50% EtOAc in hexanes to 5% MeOH in EtOAc as eluents), mp 232-234° C

Sources & evidence

ORD record
ord-59d822f8a46140da8edcf4e033b9238c
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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