Tetrahydrofuran → HCID 86754503, compound

HRID 618458Notes

Reaction equation

HRID 618458 reaction equation
C[CH:2]1[S:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][C:5]2[CH:12]=C3OCOC3=C[C:4]=2[C:3]1=O.N[C@@H](CO)[C@H:22](C1C=CC=CC=1)[OH:23].[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>>[CH3:12][C@@H:5]1[CH2:6][C@H:7]([C:9]([OH:11])=[O:10])[S:8][C:2]2[CH:3]=[C:22]3[O:23][CH2:34][O:35][C:36]3=[CH:32][C:33]=2[CH2:4]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diolHCID 159224451,2,4,5-Tetrahydro-4-methyl-7,8-methylenedioxy-5-oxo-3-benzothiepin-2-carboxylic acid

Product 1

HCID 86754503HCID 86754503, compound

Procedure

In 15 mL of THF was suspended 0.5 g of a racemic mixture, 1,2,4,5-tetrahydro-4-methyl-7,8-methylenedioxy-5-oxo-3-benzothiepin-2-carboxylic acid (content 99.5%; trans compound 88.1%, cis compound 11.4%). To the suspension was added 0.3 g (1 equivalent) of (1S,2S)-2-amino-1-phenyl-1,3-propanediol, which was made into a solution, followed by crystallization. The crystals were then aged for 30 minutes at room temperature (25° C.). The crystals were collected by filtration using, for example, glass filter, washed with 5 mL of THF, followed by drying overnight at room temperature under reduced pressure to afford 0.37 g of substantially pure (2R,4S)-1,2,4,5-tetrahydro-4-methyl-7,8-methylenedioxy-5-benzothiepin-2-carboxylic acid.(1S,2S)-2-amino-1-phenyl-1,3-propanediol salt as colorless crystals [HPLC area percentage; (2R,4R):(2S,4S):(2S,4R):(2R,4S)=0.6%:0.6%:8.3%:85.6%].

Workup

  1. customfollowed by crystallization
  2. custom(25° C.)
  3. filtrationThe crystals were collected by filtration
  4. filtrationfilter
  5. washwashed with 5 mL of THF
  6. customby drying overnight at room temperature under reduced pressure

Sources & evidence

ORD record
ord-52a4f0045af24898b0fb721676ce7dbe
Source dataset
uspto-grants-1999_09
Patent number
US05952512

Reaction notes

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