Hexane → HCID 131731109, compound

HRID 1916030Notes

Reaction equation

HRID 1916030 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:13]([O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:14])[C@@H:3]([CH3:12])[O:4]CC1C=CC=CC=1.CCCCCC>CCOC(C)=O.[Pd]>[NH:1]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C@H:2]([C:13]([O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:14])[C@@H:3]([CH3:12])[OH:4]

Participants

5

Reactant 2

HCID 8058HexaneHCID 131731108HCID 131731108, compound

Product 1

HCID 131731109HCID 131731109, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd/C (3.3 g) was added to a stirring solution of Boc-Thr(Bzl)-OcHex (11 g, 30 mmol) in AcOEt (80 mL), and the reaction mixture was vigorously stirred under a hydrogen atmosphere for overnight. The catalyst was filtered off through Celite and the solvent was removed in vacuo. The residue was purified by silica gel column chromatography, at first with AcOE:hexane 1:4 and then the desired product was washed out by AcOE:hexane 1:1 to give pure Boc-Thr-OcHex (8.6 g, 28 mmol, 94%). 1H NMR (CDCl3 400 MHz) b 5.26 (br. d, 1H), 4.89-4.82 (m, 1H), 4.30-4.20 (m, 2H), 1.94 (d, J=5.6 Hz, 1H), 1.86-1.83 (m, 2H), 1.74-1.70 (m, 2H), 1.57-1.48 (m, 3H), 1.46 (s, 9H), 1.44-1.30 (m, 3H), 1.25 (d, J=6.4 Hz, 3H).

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washat first with AcOE:hexane 1:4 and then the desired product was washed out by AcOE

Sources & evidence

ORD record
ord-4bebee759d2641ac9ae0201ef557d49e
Source dataset
uspto-grants-2013_12
Patent number
US08618049B2

Reaction notes

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