Mercapto-ethanol → HCID 178468104, compound

HRID 2398511Notes

Reaction equation

HRID 2398511 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:18]([NH:20][C@H:21]([C:32]([NH:34][C@H:35]([C:38]([NH:40][C@H:41]([C:50]([NH:52][C@@H:53]([C:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:79]([N:81]1[CH2:90][CH2:89][CH2:88][C@H:82]1[C:83]([NH:85][CH2:86][CH3:87])=[O:84])=[O:80])[CH2:72][CH2:73][CH2:74][NH:75][C:76](=[NH:78])[NH2:77])=[O:69])[CH2:64][CH:65]([CH3:67])[CH3:66])=[O:61])[CH2:54][O:55]C(C)(C)C)=[O:51])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1)=[O:39])[CH2:36][OH:37])=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].[CH3:91][C:92]([CH2:94][C:95]([OH:97])=[O:96])=[O:93].SC(O)C>FC(F)(F)C(O)=O>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:18]([NH:20][C@H:21]([C:32]([NH:34][C@H:35]([C:38]([NH:40][C@H:41]([C:50]([NH:52][C@@H:53]([C:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:79]([N:81]1[CH2:90][CH2:89][CH2:88][C@H:82]1[C:83]([NH:85][CH2:86][CH3:87])=[O:84])=[O:80])[CH2:72][CH2:73][CH2:74][NH:75][C:76](=[NH:77])[NH2:78])=[O:69])[CH2:64][CH:65]([CH3:67])[CH3:66])=[O:61])[CH2:54][OH:55])=[O:51])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1)=[O:39])[CH2:36][OH:37])=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7].[CH3:91][C:92]([CH2:94][C:95]([OH:97])=[O:96])=[O:93]

Participants

4

Reactant 2

HCID 4713212Mercapto-ethanolHCID 178468103HCID 178468103, compound

Product 1

HCID 178468104HCID 178468104, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

200 mg of Glu-His-Trp-Ser-Tyr-D-Ser(But)-Leu-Arg-Pro-NH-C2H5 -diacetate were dissolved with 0.1 ml of mercaptoethanol in 2 ml of trifluoroacetic acid. The solution was allowed to stand for 1 hour at room temperature, it was concentration and the residue was triturated with ether. The substance was suction-filtered and washed with ether, dissolved in water and chromatographed over Dowex 1×2 (acetate form). The eluate was concentrated and the residue was purified in analogy to Example 1 e) on Sephadex LH 20. Yield: 120 mg. The content of peptide base was 77.5% as per UV-spectrum [-α]D20 = -43.7° (c=1, H2O).

Workup

  1. concentrationconcentration
  2. customthe residue was triturated with ether
  3. filtrationThe substance was suction-filtered
  4. washwashed with ether
  5. dissolutiondissolved in water
  6. customchromatographed over Dowex 1×2 (acetate form)
  7. concentrationThe eluate was concentrated
  8. customthe residue was purified in analogy to Example 1 e) on Sephadex LH 20
  9. custom= -43.7° (c=1, H2O)

Sources & evidence

ORD record
ord-97607985faf441b898ee8c2f82873dae
Source dataset
uspto-grants-1977_05
Patent number
US04024248

Reaction notes

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