Water → HCID 73909622, compound

HRID 589256Notes

Reaction equation

HRID 589256 reaction equation
[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:5]([NH:7][C@H:8]([C:19]([O:21]C)=[O:20])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:6])[CH2:3][OH:4].O>CC(O)(C)C>[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C@H:2]([C:5]([NH:7][C@H:8]([C:19]([OH:21])=[O:20])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:6])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 962WaterHCID 131731745HCID 131731745, compound

Product 1

HCID 73909622HCID 73909622, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In a second step, enzymatic hydrolysis of Z-Ser-Trp-OMe was accomplished using Alcalase 2.5L DX (Int. J. Peptide Protein Res. 1990, 52) and subsequent catalytic hydrogenolysis provided the desired peptide as an off-white solid. To that end the purified Z-Ser-Trp-OMe was dissolved in tBuOH and water and Alcalase 2.5 L DX (Novozymes, Bagsvaerd, Denmark) was added. The mixture was stirred until (almost) all starting material was consumed. The mixture was then concentrated in vacuo and the residue taken up in water of pH 7. The aqueous mixture was extracted with ethyl acetate to remove any remaining starting material and subsequently the aqueous phase was acidified. The desired product, i.e. Z-Ser-Trp-OH, was isolated by extraction with ethyl acetate; the extract was dried over sodium sulphate and concentrated in vacuo.

Workup

  1. customwas consumed
  2. concentrationThe mixture was then concentrated in vacuo
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. customto remove

Sources & evidence

ORD record
ord-023a6beb1cd142338cc92b8070a12fc5
Source dataset
uspto-grants-2016_01
Patent number
US09228219B2

Reaction notes

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