Potassium Hydroxide → HCID 131721922, compound

HRID 2269602Notes

Reaction equation

HRID 2269602 reaction equation
[NH:1]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:2][C:3]([NH:5][C@H:6]([C:11]([N:13]1[CH2:28][CH2:27][CH2:26][C@H:14]1[C:15]([O:17]C(C1C=CC=CC=1)=O)=[O:16])=[O:12])[CH2:7][CH2:8][CH2:9][CH3:10])=[O:4].[OH-].[K+]>O.C1COCC1>[NH:1]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:2][C:3]([NH:5][C@H:6]([C:11]([N:13]1[CH2:28][CH2:27][CH2:26][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])[CH2:7][CH2:8][CH2:9][CH3:10])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 131721923HCID 131721923, compound

Product 1

HCID 131721922HCID 131721922, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Boc-Gly-Nleu-Pro-OBz (7.9 g, 0.0166 mol.) was dissolved in a mixture of 50 ml H2O and 80 ml THF. The solution was chilled to 0° C. KOH (1.9 g, 0.033 mol.) dissolved in 30 ml H2O was added while stirring the solution. The stirring was continued at room temperature for one hour. The THF was removed under reduced pressure. The aqueous solution was chilled to 0° C. and acidified to about pH=3 by addition of concentrated HCl (swirling the solution vigorously at the same time). The product was extracted from the aqueous solution by ethyl acetate. The combined organic layer was dried using Na2SO4 and the ethyl acetate was removed under reduced pressure to obtain the product (5.7 g, 89%). TLC Rf=0.38 (developing solvents: CMA, 85:15:3). FAB-MS, observed (M+H)+=386. 1H-NMR (500 MHz, DMSO-d6, 27° C., assignment by TOCSY) δ6.69 (m, Gly-NH), 6.57 (m, Gly-NH), 4.56 (m, Pro-α), 4.28-4.14 (m, Pro-α), 4.14-3.97 (m, Nleu-α), 3.83-3.62 (m, Gly-α), 3.62-3.44 (m, Gly-α, Pro-δ), 3.44-3.28 (m, Pro-δ), 3.12-2.92 (m, Nleu-β), 2.23-1.58 (m, Pro-β, Pro-γ, Nleu-γ), 1.34 (m, Boc-CH3), 0.85 (m, Nleu-δ), 0.78 (m, Nleu-δ).

Workup

  1. additionwas added
  2. customThe THF was removed under reduced pressure
  3. temperatureThe aqueous solution was chilled to 0° C.
  4. additionacidified to about pH=3 by addition of concentrated HCl (
  5. extractionThe product was extracted from the aqueous solution by ethyl acetate
  6. customThe combined organic layer was dried
  7. customthe ethyl acetate was removed under reduced pressure

Sources & evidence

ORD record
ord-878700c93f87450eb5c2bf53d9bfd65e
Source dataset
uspto-grants-2001_12
Patent number
US06329506B1

Reaction notes

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