HCID 131714439, compound → HCID 131714438, compound

HRID 1583843Notes

Reaction equation

HRID 1583843 reaction equation
[C:1]([N:8](C)[C@H:9]([C:14]([NH:16][C@H:17]([C:21]([N:23]([CH3:43])[C@H:24]([C:29]([NH:31][C@H:32]([C:34]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35])[CH3:33])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[NH:8]([CH3:1])[C@H:9]([C:14]([NH:16][C@H:17]([C:21]([N:23]([CH3:43])[C@H:24]([C:29]([NH:31][C@H:32]([C:34]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35])[CH3:33])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13]

Participants

3

Reactant 1

HCID 131714439HCID 131714439, compound

Product 1

HCID 131714438HCID 131714438, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

31.27 g (49.5 mMol) BOC-MeLeu-Val-MeLeu-Ala-Bzl dissolved in 100 ml trifluoroacetic acid are stirred for 21/2 hrs. at room temperature and the product solution concentrated under vacuum. The residue is diluted with 500 ml methylene carbonate solution, ice being added and the aqueous phases extracted with 200 ml methylene chloride. The combined organic phases are dried over potassium carbonate, filtered and concentrated to yield the title compound: rotation [α]D22 =-114.4° (c=1.0 in chloroform), M.P. on re-crystallisation from ether/petrol ether=66°-67°

Workup

  1. concentrationat room temperature and the product solution concentrated under vacuum
  2. additionThe residue is diluted with 500 ml methylene carbonate solution, ice being
  3. additionadded
  4. extractionthe aqueous phases extracted with 200 ml methylene chloride
  5. dry with materialThe combined organic phases are dried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3621103d4ab1410b84e9e2c576c1305a
Source dataset
uspto-grants-1985_11
Patent number
US04554351

Reaction notes

Loading…