Hydrochloric Acid → HCID 131711087, compound

HRID 2083813Notes

Reaction equation

HRID 2083813 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.C(OCC)C>C1COCC1.C(OCC)(=O)C>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 131711088HCID 131711088, compound

Product 1

HCID 131711087HCID 131711087, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

BOC-Thr(Bzl)-Tyr(Bzl)-Pro-OBzl (14.2 g.) was dissolved in THF (30 ml.), and 1 N NaOH solution (23 ml.) was added dropwise for 15 minutes at -5° C. After stirring for 4 hours at room temperature, the pH was adjusted to 7 with 1 N HCl addition, then the mixture was concentrated in vacuo to remove THF. Water was added to the aqueous layer and after washing with ethyl ether, the pH of the water layer was adjusted to pH 2 by adding 1 N HCl, then extracted twice with ethyl acetate. The ethyl acetate layer was washed with water and dried by anhydrous magnesium sulfate and concentrated in vacuo. The residue was crystallized from ethyl ether - n-hexane to obtain crude material (12 g.). This crude material was dissolved in ethyl acetate, ethyl ether added thereto and the solution was set aside to crystallize by gradual addition of n-hexane to give BOC-Thr(Bzl)-Tyr(Bzl)-Pro-OH (10.5 g., Yield: 84%, m.p.: 136° - 138° C.). TLC: one spot, Rf1 = 0.68, Rf5 = 0.63.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto remove THF
  3. additionWater was added to the aqueous layer
  4. washafter washing with ethyl ether
  5. additionby adding 1 N HCl
  6. extractionextracted twice with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried by anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized from ethyl ether - n-hexane
  11. customto obtain crude material (12 g.)
  12. customto crystallize by gradual addition of n-hexane

Sources & evidence

ORD record
ord-d0b51f2cf7354d609702b480d5efb9be
Source dataset
uspto-grants-1978_04
Patent number
US04086221

Reaction notes

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