Hydrochloric Acid → HCID 131711087, compound

HRID 256495Notes

Reaction equation

HRID 256495 reaction equation
[NH:1]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[C@H:2]([C:13]([NH:15][C@H:16]([C:32]([N:34]1[CH2:48][CH2:47][CH2:46][C@H:35]1[C:36]([O:38]CC1C=CC=CC=1)=[O:37])=[O:33])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C1COCC1>[NH:1]([C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])[C@H:2]([C:13]([NH:15][C@H:16]([C:32]([N:34]1[CH2:48][CH2:47][CH2:46][C@H:35]1[C:36]([OH:38])=[O:37])=[O:33])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:20][CH:19]=1)=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131711088HCID 131711088, compound

Product 1

HCID 131711087HCID 131711087, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.60 g of BOC-Thr(Bzl)-Tyr(Bzl)-Pro-OBzl dissolved in 20 ml of THF was mixed under cooling and stirring with 5.83 ml of 1N sodium hydroxide, and the mixture was stirred at room temperature for 3 hours. Then, 1N hydrochloric acid was added to adjust pH to 7, and the mixture was concentrated under reduced pressure to evaporate THF. The residual aqueous solution was diluted with water, washed with diethyl ether, then adjusted to pH 2 with addition of 1N hydrochloric acid and extracted twice with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diethyl ether-n-hexane to obtain a crude product. Recrystallization of this product from ethyl acetate-diethyl ether-n-hexane gave 2.15 g (yield: 67.8%) of BOC-Thr(Bzl)-Tyr(Bzl)-Pro-OH melting at 134° to 137° C. Rf1 =0.46, Rf3 =0.24.

Workup

  1. additionwas mixed
  2. temperatureunder cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customto evaporate THF
  5. additionThe residual aqueous solution was diluted with water
  6. washwashed with diethyl ether
  7. additionadjusted to pH 2 with addition of 1N hydrochloric acid
  8. extractionextracted twice with ethyl acetate
  9. washThe ethyl acetate layer was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was crystallized from diethyl ether-n-hexane
  13. customto obtain a crude product
  14. customRecrystallization of this product from ethyl acetate-diethyl ether-n-hexane

Sources & evidence

ORD record
ord-3bfeab3c6c104e8ba34fdc4e17fcff97
Source dataset
uspto-grants-1987_10
Patent number
US04703106

Reaction notes

Loading…