Hexane → HCID 58844211, compound

HRID 1271101Notes

Reaction equation

HRID 1271101 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][OH:25])[CH:19]=1)=[C:8]2[C:12]([O:14]CC=C)=[O:13])[CH3:3].C(C(CCCC)C([O-])=O)C.[Na+:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][OH:25])[CH:19]=1)=[C:8]2[C:12]([O-:14])=[O:13])[CH3:3].[Na+:36]

Participants

7

Reactant 4

HCID 8058HexaneHCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 58844833HCID 58844833, compound

Product 1

HCID 58844211HCID 58844211, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-(hydroxymethyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate prepared in the above step, sodium 2-ethylhexanoate (242 mg) and triphenylphosphine (32 mg) were dissolved in THF (10 ml), and the solution was cooled to 0° C. Thereto tetrakis(triphenylphosphine) palladium(0) (70 mg) was added. Thirty minutes later, thereto hexane (3 ml) was added and then the solution was stirred for additional 30 minutes. The resulting crystals were filtered under nitrogen atmosphere, and dried under reduced pressure to give sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-(hydroxymethyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (217 mg).

Workup

  1. filtrationThe resulting crystals were filtered under nitrogen atmosphere
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-47d0a1aa0459425b9ac45b840fd95e4c
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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