Trifluoroacetic acid → HCID 131711082, compound

HRID 2083810Notes

Reaction equation

HRID 2083810 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH2:19])=[O:18])=[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.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]>>[NH2:1][C@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH2:19])=[O:18])=[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.[F:33][C:32]([C:30]([OH:36])=[O:31])([F:35])[F:34]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131711083HCID 131711083, compound

Product 1

HCID 131711082HCID 131711082, compound

Procedure

BOC-Thr(Bzl)-Pro-NH2 (10.0 g.) was added to TFA (30 ml.) at -5° C., stirred for 30 minutes, and concentrated in vacuo. The residue was treated with ether, filtered and dried over sodium to obtain H-Thr(Bzl)-Pro-NH2.TFA. BOC-Ala-Gly-OH obtained in (3) (6.08 g.) and HOBT (3.34 g.) were added in THF (100 ml.) and WSC (4.5 ml.) was added thereto at -5° C. (pH 4.0). After stirring at -5° C. for 1 hour and at room temperature for 7 hours, the mixture was cooled at -5° C., WSC (0.8 ml.) added and the pH adjusted to 4.0, and stirred at -5° C. for 1 hour and at room temperature overnight, and concentrated in vacuo. The residue was dissolved in ethyl acetate (400 ml.), washed with saturated sodium chloride solution, twice with 5% aqueous sodium bicarbonate (100 ml.), 1 N HCl saturated with NaCl (100 ml.) and water (50 ml.), in this order.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with ether
  3. filtrationfiltered
  4. dry with materialdried over sodium

Sources & evidence

ORD record
ord-0f317a5e929447f193ac3c2895a029ac
Source dataset
uspto-grants-1978_04
Patent number
US04086221

Reaction notes

Loading…