Tetrahydrofuran → HCID 67137782, compound

HRID 1743237Notes

Reaction equation

HRID 1743237 reaction equation
[CH2:1]([C@:4]1([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8](=O)O[C@@H](C(C)(C)C)[N:5]1C(OCC=C)=O)[CH:2]=[CH2:3].N1C[CH2:31][O:30]CC1.[O:33]1CCCC1>>[NH2:5][C@:4]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH2:1][CH:2]=[CH2:3])[CH2:8][C:31]([OH:30])=[O:33]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 69793034HCID 69793034, compound

Product 1

HCID 67137782HCID 67137782, compound

Procedure

A mixture of 2 g of allyl (2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxooxazolidine-3-carboxylate, 60 ml of tetrahydrofuran, 4.88 ml of morpholine and 300 mg of tetrakis-triphenylphosphinepalladium is stirred at room temperature for 20 minutes and then concentrated in vacuo. The residue is stirred in a mixture of 6 ml of glacial acetic acid and 20 ml of water for 30 minutes. After the volatile constituents have been stripped off in vacuo at 40° C., the product is purified by column chromatography (silica gel, mobile phase: methylene chloride:methanol=9:1).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe residue is stirred in a mixture of 6 ml of glacial acetic acid and 20 ml of water for 30 minutes
  3. customhave been stripped off in vacuo at 40° C.
  4. customthe product is purified by column chromatography (silica gel, mobile phase: methylene chloride:methanol=9:1)

Sources & evidence

ORD record
ord-1f497cbff88f4286aa69b96ead4da537
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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