Hydrochloric Acid → N-Benzyloxycarbonyl-L-isoleucyl-O-t-butyl-L-threonyl-O-t-butyl-L-threonyl-Nepsilon-t-butyloxycarbonyl-L-lysine

HRID 2164492Notes

Reaction equation

HRID 2164492 reaction equation
[NH:1]([C:54]([O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:55])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:29]([NH:31][C@H:32]([C:45]([O:47]C1C=CC=CC=1)=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:30])[C@@H:22]([CH3:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:19])[C@@H:11]([CH3:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].O.OO.Cl>CC(C)=O.CO.CC(O)=O>[CH2:57]([O:56][C:54]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:29]([NH:31][C@H:32]([C:45]([OH:47])=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])=[O:30])[C@@H:22]([CH3:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:19])[C@@H:11]([CH3:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4])=[O:55])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 131714167Z-Ile-Thr(tBu)-Thr(tBu)-Lys(Boc)-OPh

Product 1

HCID 131714166N-Benzyloxycarbonyl-L-isoleucyl-O-t-butyl-L-threonyl-O-t-butyl-L-threonyl-Nepsilon-t-butyloxycarbonyl-L-lysine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 887MethanolSolvent2×

Procedure

Z-Ile-Thr(tBu)-Thr(tBu)-Lys(Boc)-OPh (0.884 g, 1.0 mmol) was dissolved in 25 ml acetone and 4 ml H2O added followed by the addition of 3% H2O2 (1.16 ml, 1.0 mmol) and the solution stirred magnetically. The pH was adjusted to, and maintained at, 10.5 by the addition of 0.1N NaOH(a) after stirring at pH 10.5 for 1.5 h, 0.1N HCl was added until the reaction mixture reached pH 3. The white solid which formed was collected by filtration,(b) washed with H2O (~60 ml) and dried in vacuo to yield 0.781 g (96.6%); mp 174°-176° dec;(c)Rf 0.63 (ChCl3 :CH3OH:AcOH; 80-5-1); [α]D25 +13.66 (c 1, CH3OH). Anal: calc. for C41H69N5O11 (808.0): C, 60.94; H, 8.61; N, 8.67. Found: C, 60.83; H, 8.70; N, 8.93.

Workup

  1. temperaturemaintained at, 10.5
  2. stirringafter stirring at pH 10.5 for 1.5 h
  3. customThe white solid which formed
  4. filtrationwas collected by filtration,(b)
  5. washwashed with H2O (~60 ml)
  6. customdried in vacuo
  7. customto yield 0.781 g (96.6%)

Sources & evidence

ORD record
ord-96e4906261c44339a3232cd0340a8d5a
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

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