Trifluoroacetic acid → HCID 131711084, compound

HRID 2083812Notes

Reaction equation

HRID 2083812 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([NH2:28])=[O:27])=[O:23])[C@@H:12]([CH3:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:9])=[O:5])[CH3:3].[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>>[NH2:1][C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([NH2:28])=[O:27])=[O:23])[C@@H:12]([CH3:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:9])=[O:5])[CH3:3].[F:42][C:41]([C:39]([OH:45])=[O:40])([F:44])[F:43]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131711086HCID 131711086, compound

Product 1

HCID 131711084HCID 131711084, compound

Procedure

BOC-Ala-Gly-Thr(Bzl)-Pro-NH2 (10.5 g.) was added to TFA (35 ml.) at -5° C., and, after stirring for 30 minutes, concentrated in vacuo. The residue was treated with ethyl ether, and the precipitated material was filtered and dried in vacuo over sodium hydroxide to obtain H-Ala-Gly-Thr(Bzl)-Pro-NH2.TFA. THF (100 ml.) was added thereto, and triethylamine was added at -5° C. to adjust the pH to 5.0. BOC-Val-Gly-OH (5.49 g.) and HOBT (2.66 g.) were added thereto. To this mixture WSC (3.61 ml.) was added dropwise at -5° C., and the mixture stirred at -5° C. for 1 hour and at room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue was dissolved in chloroform (300 ml.). The solution was washed twice with NaCl-saturated 1 N HCl (200 ml.), twice with NaCl saturated 5% sodium bicarbonate solution (200 ml.) and saturated NaCl solution (75 ml.) in this order. After the solution was dried with anhydrous sodium sulfate, the organic layer was concentrated in vacuo. Recrystallization from methanol - ethyl ether gave BOC-Val-Gly-Ala-Gly-Thr(Bzl)-Pro-NH2 (12.0 g., Yield: 88.3%). m.p.: 121° - 135° C. (decomp.). TLC: one spot. (solvent system 6).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with ethyl ether
  3. filtrationthe precipitated material was filtered
  4. dry with materialdried in vacuo over sodium hydroxide

Sources & evidence

ORD record
ord-eff8faa74a6741bea49c8e8530cfe567
Source dataset
uspto-grants-1978_04
Patent number
US04086221

Reaction notes

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