Ethanol → Boc-ala-ala-pro-OH

HRID 1458185Notes

Reaction equation

HRID 1458185 reaction equation
C([O:8][C:9](=[O:32])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:31])[C@H:16]([CH3:30])[NH:17][C:18](=[O:29])[C@H:19]([CH3:28])[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])C1C=CC=CC=1.[H][H].C(O)C>C(O)(C)(C)C>[C:21]([NH:20][C@H:19]([C:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:32])=[O:8])=[O:31])[CH3:30])=[O:29])[CH3:28])([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 15289361Boc-AlaAlaPro-OBzlHCID 178418361HCID 178418361, compound

Product 1

HCID 11902955Boc-ala-ala-pro-OHYield 98%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A Parr flask was flushed with argon and charged with 10% palladium on charcoal (0.74 g), followed by the addition of Boc-L-alanyl-L-alanyl-L-proline benzyl ester (1.8 g, 4.0 mmol) dissolved in tert-butanol (300 ml). The reaction mixture shaken under 30 psi of hydrogen at 35° C. for 5 hr. After cooling to room temperature, ethanol (50 ml) was added and the solution was filtered through celite and the filtrate concentrated on a rotary evaporator. The residue was azeotroped with chloroform-hexane to remove the last traces of tert-butanol and then dried under high vacuum to give Boc-L-alanyl-L-alanyl-L-proline (1.40 g, 3.9mmol) in 98% yield.

Workup

  1. customA Parr flask was flushed with argon
  2. additioncharged with 10% palladium on charcoal (0.74 g)
  3. filtrationthe solution was filtered through celite
  4. concentrationthe filtrate concentrated on a rotary evaporator
  5. customThe residue was azeotroped with chloroform-hexane
  6. customto remove the last traces of tert-butanol
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-b968e0638a724fe79697b62e9c652bbf
Source dataset
uspto-grants-1998_12
Patent number
US05849866

Reaction notes

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