Trifluoroacetic acid → HCID 131711578, compound

HRID 971852Notes

Reaction equation

HRID 971852 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:21][OH:22])=[O:18])[C@@H:14]([CH3:16])[OH:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:21][OH:22])=[O:18])[C@@H:14]([CH3:16])[OH:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[F:34][C:35]([C:36]([OH:38])=[O:37])([F:40])[F:39]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131711580HCID 131711580, compound

Product 1

HCID 131711578HCID 131711578, compound

Conditions

Temperature
25 °C

Procedure

BOC-Phe-Thr-Ser-OMe, 6.63 g., is suspended in 67 ml. of trifluoroacetic acid. The mixture is stirred at 25° C. until solution is complete. The solution is cooled to 0° C. and the product precipitated by the addition of 300 ml. of ether and 600 ml. of petroleum ether. The product is filtered, washed with ether:petroleum ether and dried in vacuo. The yield of substantially pure Phe-Thr-Ser-OMe.TFA is 6.4 g.

Workup

  1. temperatureThe solution is cooled to 0° C.
  2. customthe product precipitated by the addition of 300 ml
  3. filtrationThe product is filtered
  4. washwashed with ether
  5. dry with materialpetroleum ether and dried in vacuo

Sources & evidence

ORD record
ord-4505a0c0ea0d483580a7e9f1e099023a
Source dataset
uspto-grants-1979_07
Patent number
US04161521

Reaction notes

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