Hydrochloric Acid → HCID 178434315, compound

HRID 1786653Notes

Reaction equation

HRID 1786653 reaction equation
C([O:5][C:6](=[O:37])[NH:7][CH:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:9]([OH:29])[CH2:10][N:11]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[C:18]2[CH3:24])(=[O:14])=[O:13])(C)(C)C.Cl.C(N(C(C)C)CC)(C)C.[O:48]1[CH:52]2[O:53][CH2:54][CH2:55][CH:51]2[CH:50](OC(=O)ON2C(=O)CCC2=O)[CH2:49]1>O1CCOCC1>[O:48]1[CH:52]2[O:53][CH2:54][CH2:55][CH:51]2[CH:50]([O:5][C:6](=[O:37])[NH:7][CH:8]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:9]([OH:29])[CH2:10][N:11]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[CH3:24])(=[O:13])=[O:14])[CH2:49]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 17981482Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl esterHCID 178434316HCID 178434316, compound

Product 1

HCID 178434315HCID 178434315, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

{1-Benzyl-2-hydroxy-3-[isobutyl-(3-methyl-1H-indazole-5-sulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester (25 mg, 0.047 mmol) was added to a solution of 4N HCl in dioxane (0.25 mL). Material precipitated out so 800 uL conc. HCl was added and the reaction heated at reflux for 2 h. The resulting solution was concentrated under vacuum and concentrated 2 additional times from 1 mL methylene chloride. This crude amine was dissolved in 0.5 mL methylene chloride and diisopropylethylamine (80 uL, 0.46 mmol) was then added. To this solution was added carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (16 mg, 0.055 mmol) and the reaction stirred overnight. The reaction was concentrated under vacuum and purified by preparative HPLC. MS 587 (MH+).

Workup

  1. customMaterial precipitated out so 800 uL conc. HCl
  2. additionwas added
  3. temperaturethe reaction heated
  4. temperatureat reflux for 2 h
  5. concentrationThe resulting solution was concentrated under vacuum
  6. concentrationconcentrated 2 additional times from 1 mL methylene chloride
  7. dissolutionThis crude amine was dissolved in 0.5 mL methylene chloride
  8. concentrationThe reaction was concentrated under vacuum
  9. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ce026a901f9f47dc966a3a7150cbc0c2
Source dataset
uspto-grants-2009_03
Patent number
US07507763B2

Reaction notes

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