Water → HCID 131713587, compound

HRID 1462852Notes

Reaction equation

HRID 1462852 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:19]([NH:21][C@H:22]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])=[O:20])[CH2:3][C:4]1[N:8]=[CH:7][N:6]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=1.S(O)(C1C=CC(C)=CC=1)(=O)=O.O.O>O1CCOCC1>[NH2:1][C@H:2]([C:19]([NH:21][C@H:22]([C:38]([O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39])[CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])=[O:20])[CH2:3][C:4]1[N:8]=[CH:7][N:6]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 131713588HCID 131713588, compound

Product 1

HCID 131713587HCID 131713587, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.0 g of Boc-His(Tos)-Lys(Z)-OBzl was added to 9.8 g of TosOH.H2O dissolved in 26 of dioxane, which was then left at room temperature for an hour with occasional shaking. Next, water was added to it and the mixture was extracted with ethyl acetate. The extract was washed with sodium bicarbonate aqueous solution and saturated saline, and dried over sodium sulfate anhydride. Thereafter, the solvent was distilled off to obtain 3.75 g of His(Tos)-Lys(Z)-OBzl as a pale brown oily matter.

Workup

  1. waitwas then left at room temperature for an hour with occasional shaking
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with sodium bicarbonate aqueous solution and saturated saline
  4. dry with materialdried over sodium sulfate anhydride
  5. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-ab62077494914e08bc8e63cea5dcb9ab
Source dataset
uspto-grants-1984_07
Patent number
US04461724

Reaction notes

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