Diethyl Ether → H-Leu-Ser-Thr-OBzl.TFA

HRID 971580Notes

Reaction equation

HRID 971580 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:13]([NH:15][C@H:16]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@@H:17]([CH3:19])[OH:18])=[O:14])[CH2:11][OH:12])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].CCOCC.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:13]([NH:15][C@H:16]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@@H:17]([CH3:19])[OH:18])=[O:14])[CH2:11][OH:12])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[F:42][C:43]([C:44]([OH:46])=[O:45])([F:48])[F:47]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 131711574BOC-Leu-Ser-Thr-OBzl

Product 1

HCID 131710003H-Leu-Ser-Thr-OBzl.TFA

Procedure

46.1 g of BOC-Leu-Ser-Thr-OBzl are dissolved in 92.5 ml of 90% strength trifluoroacetic acid and left for 1 hour at 20° C. Thereafter dry ether (925 ml) is added whilst stirring, and the mixture is stirred for one hour at 0° C. and left to stand overnight at -10° C. The resulting precipitate is filtered off, washed three times with dry ether and dried in vacuo over sodium hydroxide. Melting point 168°-171° C.; Rf7 = 0.80 (on silica gel).

Workup

  1. stirringthe mixture is stirred for one hour at 0° C.
  2. waitleft
  3. waitto stand overnight at -10° C
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed three times with dry ether
  6. dry with materialdried in vacuo over sodium hydroxide

Sources & evidence

ORD record
ord-1b19416b17fd42bea7bbda5870d91ef0
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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