Hydrazine hydrate (1:1) → HCID 131714604, compound

HRID 246920Notes

Reaction equation

HRID 246920 reaction equation
[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:25]([NH:27][C@H:28]([C:33]([NH:35][C@H:36]([C:39](OC)=[O:40])[CH2:37][OH:38])=[O:34])[CH2:29][C:30](=[O:32])[NH2:31])=[O:26])[C@@H:22]([CH3:24])[OH:23])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].[OH2:50].[NH2:51][NH2:52]>CN(C=O)C.CO>[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:47])[CH3:48])=[O:44])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:25]([NH:27][C@H:28]([C:33]([NH:35][C@H:36]([C:37]([NH:51][NH2:52])=[O:38])[CH2:39][OH:40])=[O:34])[CH2:29][C:30](=[O:32])[NH2:31])=[O:26])[C@@H:22]([CH3:24])[OH:23])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:50])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 131714602HCID 131714602, compound

Product 1

HCID 131714604HCID 131714604, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5 g of Boc-Ile-Phe-Thr-Asn-Ser-OMe (7.2 mM) in 40 ml of DMF and 200 ml of methanol cooled on an ice bath has 3.6 ml of an 80% solution of hydrazine hydrate added thereto. After 21 hours of reaction at ambient temperature, 0.9 ml of the same solution of hydrazine hydrate are added. After 3 more hours, the gel obtained is filtered, washed with methanol and dried in vacuo. 3.94 g of product are obtained.

Workup

  1. additionadded
  2. customAfter 21 hours of reaction at ambient temperature
  3. customAfter 3 more hours, the gel obtained
  4. filtrationis filtered
  5. washwashed with methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5d0590ebf2b94dc884e8f6cf41403a32
Source dataset
uspto-grants-1987_11
Patent number
US04704450

Reaction notes

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