Sulfuric Acid → HCID 68615882, compound

HRID 984028Notes

Reaction equation

HRID 984028 reaction equation
[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:20][NH:21][C:22](=[O:40])[C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]4[NH:34][CH2:35][CH2:36][CH2:37][N:38]=4)=[CH:25][CH:24]=3)[C:17]([OH:19])=[O:18])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(=O)(=O)(O)O.[CH:46]([OH:49])([CH3:48])[CH3:47]>>[C:17]([OH:19])(=[O:18])[CH3:16].[CH:46]([O:49][C:17](=[O:18])[C@@H:16]([NH:15][C:13]([O:12][CH2:11][C:1]12[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2)=[O:14])[CH2:20][NH:21][C:22](=[O:40])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]2[NH:38][CH2:37][CH2:36][CH2:35][N:34]=2)=[CH:25][CH:24]=1)([CH3:48])[CH3:47]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 11410286HCID 11410286, compound

Product 1

HCID 68615882HCID 68615882, compound

Procedure

17.5 g of (2S)-2-(adamantan-1-ylmethoxycarbonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionic acid were dissolved in 670 ml of isopropanol. 1.8 ml of concentrated sulfuric acid were added and the reaction mixture was refluxed for 24 h. The solvent was distilled off in vacuo, the residue was brought to pH 7 with an aqueous solution of sodium chloride and solid sodium bicarbonate and the mixture was extracted four times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, the ethyl acetate was distilled off, the residue was treated with 20 ml of glacial acetic acid and lyophilized.

Workup

  1. temperaturethe reaction mixture was refluxed for 24 h
  2. distillationThe solvent was distilled off in vacuo
  3. extractionthe mixture was extracted four times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. distillationthe ethyl acetate was distilled off
  6. additionthe residue was treated with 20 ml of glacial acetic acid

Sources & evidence

ORD record
ord-617f5a68b1584c43afa449824b5b85f0
Source dataset
uspto-grants-2005_03
Patent number
US06867213B2

Reaction notes

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