Sodium Hydroxide → N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-hydroxy-2-(3-formamido-4-benzyloxyphenyl) ethylamine

HRID 501997Notes

Reaction equation

HRID 501997 reaction equation
[OH:1][C@H:2]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@H:15]([O:33][Si](C(C)(C)C)(C)C)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:18]([NH:30][CH:31]=[O:32])[CH:17]=2)=[CH:7][CH:6]=1.F.F.F.C(N(CC)CC)C.[OH-].[Na+]>O1CCCC1.C(OC(C)C)(=O)C>[OH:1][C@H:2]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@H:15]([OH:33])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:18]([NH:30][CH:31]=[O:32])[CH:17]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57755062N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-tert-butyldimethylsiloxy-2-(3-formamido4-benzyloxyphenyl)ethylamine

Product 1

HCID 57755061N-{2-[4-((R)-2-hydroxy-2-phenylethylamino)phenyl]ethyl}-(R)-2-hydroxy-2-(3-formamido-4-benzyloxyphenyl) ethylamineYield 99%

Reagents, catalysts & solvents 2

HCID 7915Isopropyl AcetateSolventHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 5 (5.2 g, 8.1 mmol) was dissolved in tetrahydrofuran (26 mL) and triethylamine trihydrofluoride (1.4 mL, 8.6 mmol) was added. The solution was stirred for 20 h. The reaction was quenched by addition of water (7.6 mL) followed by 10.0 N sodium hydroxide (3.8 mL, 38 mmol). After 3 min, the reaction was diluted with isopropyl acetate (20 mL) and transferred to a separatory funnel. The mixture was shaken and the biphasic mixture was filtered through celite to remove undissolved solids. The filtrate was returned to a separatory funnel and the phases were separated. The organic layer was washed with a mixture of 9 mL water and 9 mL saturated aqueous sodium chloride followed by 15 mL of saturated aqueous sodium chloride. The organic layer was dried over sodium sulfate and concentrated to afford the product 6 as a brown gelatinous solid (4.2 g, 8.0 mmol, 99%). m/z: [M+H+] calcd for C32H35N3O4 526.3; found 526.4.

Workup

  1. customThe reaction was quenched by addition of water (7.6 mL)
  2. waitAfter 3 min
  3. customtransferred to a separatory funnel
  4. stirringThe mixture was shaken
  5. filtrationthe biphasic mixture was filtered through celite
  6. customto remove undissolved solids
  7. customThe filtrate was returned to a separatory funnel
  8. customthe phases were separated
  9. washThe organic layer was washed with a mixture of 9 mL water and 9 mL saturated aqueous sodium chloride
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-b6dc34987f0a4882bfca2dac7bc63b89
Source dataset
uspto-grants-2010_08
Patent number
US07772434B2

Reaction notes

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