Tetrahydrofuran → HCID 58775662, compound

HRID 1945228Notes

Reaction equation

HRID 1945228 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=[O:4].[Cl:15][C:16]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:17]=1[NH:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[OH:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].[CH2:56]1[CH2:60][O:59]C[CH2:57]1>O>[Cl:15][C:16]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:17]=1[NH:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[O:34][C@@H:56]([CH3:57])[C:60]([OH:59])=[O:4]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66995709HCID 66995709, compound

Product 1

HCID 58775662HCID 58775662, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diisopropyl azodicarboxylate (0.14 ml) was added to a stirred solution of the product from example 56 step (ii) (0.2 g), triphenylphosphine (0.18 g), R-methyl lactate (0.1 g) in THF (10 ml). After 20 h, aqueous 1M sodium hydroxide solution (2 ml) was added and stirred for 4 h. The mixture was diluted with water (30 ml) then partitioned between ethyl acetate/2M hydrochloric acid. The organics were separated, washed with brine, dried and evaporated under reduced pressure. The residue was purified by RPHPLC, yield 0.094 g.

Workup

  1. customthen partitioned between ethyl acetate/2M hydrochloric acid
  2. customThe organics were separated
  3. washwashed with brine
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by RPHPLC, yield 0.094 g

Sources & evidence

ORD record
ord-105e037fe27b4048b171e24d2e17a2df
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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