Trifluoroacetic acid → Trifluoroacetic acid

HRID 1982313Notes

Reaction equation

HRID 1982313 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:92][CH2:91][CH2:90][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:89][CH2:88][CH2:87][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([NH:40][C@H:41]([C@H:46]([CH2:48][C:49]([NH:51][C@H:52]([C:57]([NH:59][C@H:60]([C:67]([NH:69][C@H:70]([C:83]([O:85][CH3:86])=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][NH:75]C(OC(C)(C)C)=O)=[O:68])[CH2:61][C:62]1[N:66]=[CH:65][NH:64][CH:63]=1)=[O:58])[C@H:53]([CH2:55][CH3:56])[CH3:54])=[O:50])[OH:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4].C(OC(C)C)(C)C.[F:107][C:108]([F:113])([F:112])[C:109]([OH:111])=[O:110]>>[NH:1]1[CH2:92][CH2:91][CH2:90][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:89][CH2:88][CH2:87][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([NH:40][C@H:41]([C@H:46]([CH2:48][C:49]([NH:51][C@H:52]([C:57]([NH:59][C@H:60]([C:67]([NH:69][C@H:70]([C:83]([O:85][CH3:86])=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][NH2:75])=[O:68])[CH2:61][C:62]1[N:66]=[CH:65][NH:64][CH:63]=1)=[O:58])[C@H:53]([CH2:55][CH3:56])[CH3:54])=[O:50])[OH:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4].[C:109]([OH:111])([C:108]([F:113])([F:112])[F:107])=[O:110]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 178455896HCID 178455896, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178455895HCID 178455895, compound

Procedure

Stage 2.7 330 mg of Boc-Pro-His-Pro-Phe-His-Sta-Ile-His-Lys(Boc)-OMe are dissolved in 1.7 ml of 95% strength trifluoroacetic acid and left to stand for 30 minutes at 25°. Then, 14 ml of diisopropyl ether are added, the whole is stirred for 30 minutes at 0°, filtered and dried in a high vacuum over KOH, yielding H-Pro-His-Pro-Phe-His-Sta-Ile-His-Lys-OMe×5 TFA; Rf (D)=0.17; Rf (K)=0.20.

Workup

  1. waitleft
  2. filtrationfiltered
  3. dry with materialdried in a high vacuum over KOH

Sources & evidence

ORD record
ord-3d3838d46cba48dca07ea62e472a1699
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

Loading…