HCID 86591188, compound → HCID 69817908, compound

HRID 2417445Notes

Reaction equation

HRID 2417445 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:41])[CH2:9][N:10]([C@@H:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29]([C:31]3[CH:32]=[C:33]4[C:37](=[CH:38][CH:39]=3)[N:36]([CH3:40])[CH:35]=[CH:34]4)=[O:30])=[CH:24][CH:23]=2)[CH2:19][OH:20])C(=O)OC(C)(C)C)[CH:5]=[CH:6][CH:7]=1>Cl.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:41])[CH2:9][NH:10][C@H:18]([CH2:19][OH:20])[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:29]([C:31]3[CH:32]=[C:33]4[C:37](=[CH:38][CH:39]=3)[N:36]([CH3:40])[CH:35]=[CH:34]4)=[O:30])=[CH:26][CH:27]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86591188HCID 86591188, compound

Product 1

HCID 69817908HCID 69817908, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

tert-Butyl N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-N-[(1S)-2-hydroxy-1-(4-[[(1-methyl-1H-indol-5-yl)carbonyl]amino]benzyl]ethyl]carbamate (101 mg) was dissolved in 4N hydrogen chloride in ethanol (1.0 ml) and the solution was stirred at room temperature for 5 hours. The solvent was removed by evaporation and the residual solid was dissolved in methanol. To the solution was added 1N sodium hydroxide solution (175 μl) and the solvent was removed by evaporation. The residue was chromatographed on silica gel (eluent: chloroform/methanol=9/1) to give N-[4-[(2S)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-hydroxypropyl]phenyl]-1-methyl-1H-indole-5-carboxamide (34.2 mg) as a pale yellow solid.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residual solid was dissolved in methanol
  3. additionTo the solution was added 1N sodium hydroxide solution (175 μl)
  4. customthe solvent was removed by evaporation
  5. customThe residue was chromatographed on silica gel (eluent: chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-e4cdd51f27b74a71bcb18dc67692bd3b
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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