1-Butanol → HCID 9954958, compound

HRID 480392Notes

Reaction equation

HRID 480392 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:53])[C:7]([S:25][C@@H:26]1[CH2:30][CH2:29][O:28][C@@H:27]1[CH2:31][NH:32][C:33](=[O:52])[C@@H:34]([NH:38]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)[CH:35]([CH3:37])[CH3:36])=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].C(O)CCC>[Pd].O>[NH2:38][C@@H:34]([CH:35]([CH3:37])[CH3:36])[C:33]([NH:32][CH2:31][C@@H:27]1[C@H:26]([S:25][C:7]2[C@H:6]([CH3:53])[C@H:5]3[N:9]([C:10](=[O:11])[C@@H:4]3[C@H:2]([OH:1])[CH3:3])[C:8]=2[C:12]([OH:14])=[O:13])[CH2:30][CH2:29][O:28]1)=[O:52]

Participants

5

Reactant 2

HCID 2631-ButanolHCID 10723809HCID 10723809, compound

Product 1

HCID 9954958HCID 9954958, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-{[(2R,3R)-2-({[(2S)-3-methyl-2-({[(4-nitrobenzyl)oxy]carbonyl}amino)-butanoyl]amino}methyl)tetrahydrofuran-3-yl]thio}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.200 g), 50% wet 10% palladium on carbon (0.256 g), 1-butanol (20 ml) and water (20 ml) is hydrogenated in a Parr apparatus at 56 psi for 8 hours. The catalyst is then removed by filtration through diatomaceous earth and washed with 2×6 ml of water. The 1-butanol layer is extracted once with 6 ml of water. The combined aqueous solution (ca. 38 ml) is extracted twice with 2×10 ml of isopropyl acetate, concentrated under reduced pressure below 28° C. to ca. 20 ml and lyophilized to give 97.1 mg (83.0%) of the desired product as a slightly tan solid. MS (ES), m/z:442.3 (M+H)+; rotation [α]D25+42±1° (c 0.84, H2O); purity by analytical HPLC (100%).

Workup

  1. customThe catalyst is then removed by filtration through diatomaceous earth
  2. washwashed with 2×6 ml of water
  3. extractionThe 1-butanol layer is extracted once with 6 ml of water
  4. extractionThe combined aqueous solution (ca. 38 ml) is extracted twice with 2×10 ml of isopropyl acetate
  5. concentrationconcentrated under reduced pressure below 28° C. to ca. 20 ml

Sources & evidence

ORD record
ord-8dbd4e9726e745f9ac2a2af2d58bb10f
Source dataset
uspto-grants-2003_11
Patent number
US06649756B2

Reaction notes

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