Potassium Hydroxide → Boc-gly-pro-OH

HRID 1870097Notes

Reaction equation

HRID 1870097 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:2][C:3]([N:5]1[CH2:20][CH2:19][CH2:18][C@H:6]1[C:7]([O:9]C(C1C=CC=CC=1)=O)=[O:8])=[O:4].[OH-].[K+]>O.C1COCC1>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:2][C:3]([N:5]1[CH2:20][CH2:19][CH2:18][C@H:6]1[C:7]([OH:9])=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 131721917HCID 131721917, compound

Product 1

HCID 11673468Boc-gly-pro-OHYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The Boc-Gly-Pro-OBz (19.4 g, 0.054 mol.) was dissolved in a mixture of 100 ml H2O and 100 ml THF. After cooling the solution to 0° C., KOH (4.8 g, 0.085 mol.) in 50 ml H2O was added slowly. The solution was stirred for one hour. Then, the THF was removed under reduced pressure and the aqueous solution was extracted with ethyl acetate to remove the benzyl alcohol. The resulting aqueous phase was covered by 200 ml ethyl acetate and was acidified at 0° C. to about pH 2 by addition of concentrated HCl slowly (vigorously swirling the solution at the same time). The product was extracted from the aqueous phase with ethyl acetate 3×200 ml. The organic layers were combined and washed with brine 2×30 ml, and dried by Na2SO4. Removal of the ethyl acetate gave the product Boc-Gly-Pro-OH (white solid, 12.3 g, 85%) TLC Rf=0.25 (CMA, 85:15:3) FAB-MS, observed MH+ =273. 1H-NMR (360 MHz, DMSO-d6, 20° C.) δ 12.55 (s, 1H, carboxyl), 6.79 (s, NH-major), 4.50 (dd, 0.25H, Pro α-minor), 4.20 (dd, 0.71H, Pro-α-major), 3.81-3.62 (m, 1.7H, Gly-α-major) 3.47-3.33 (m, 2H, Pro-δ and Gly-α-minor), 2.25-2.00 (m, 1.2H, Pro-β), 1.96-1.60 (m, 2.7H, Pro-β and Pro-γ), 1.36 (s, 9H, Boc).

Workup

  1. customThen, the THF was removed under reduced pressure
  2. extractionthe aqueous solution was extracted with ethyl acetate
  3. customto remove the benzyl alcohol
  4. additionwas acidified at 0° C. to about pH 2 by addition of concentrated HCl slowly (
  5. extractionThe product was extracted from the aqueous phase with ethyl acetate 3×200 ml
  6. washwashed with brine 2×30 ml
  7. dry with materialdried by Na2SO4
  8. customRemoval of the ethyl acetate

Sources & evidence

ORD record
ord-ab71e847fd8547ef9ecf748507014144
Source dataset
uspto-grants-2000_08
Patent number
US06096710

Reaction notes

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