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Sodium Bicarbonate → HCID 90166363, compound

HRID 1486767
Notes
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Reaction equation

HRID 1486767 reaction equation
[NH:1]([C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([C@@H:10]2[CH2:12][C@H:11]2[C:13]2[N:17]([CH3:18])[C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[N:14]=2)[CH:4]=1)[NH2:2].[Si:23]([O:30][C@@H:31]([CH3:40])[C:32]([N:34]=[C:35](N(C)C)[CH3:36])=O)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>C(O)(=O)C.COCCOC>[Si:23]([O:30][C@H:31]([C:32]1[N:1]([C:3]2[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([C@@H:10]3[CH2:12][C@H:11]3[C:13]3[N:17]([CH3:18])[C:16]4[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=4[N:14]=3)[CH:4]=2)[N:2]=[C:35]([CH3:36])[N:34]=1)[CH3:40])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 86732071HCID 86732071, compoundHCID 90157317(S)-2-((tert-butyldimethylsilyl)oxy)-N-(1-(dimethylamino)ethylidene)propanamide

Product 1

HCID 90166363HCID 90166363, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 8071
1,2-Dimethoxyethane
Solvent

Procedure

To a solution of Intermediate 6 (1.8 g, 6.1 mmol) in acetic acid (40 ml) was added Intermediate 13 (4.0 g, 14.7 mmol) as a crude reaction mixture in 1,2-dimethoxyethane (40 mL). The reaction mixture was allowed to stir for 5 minutes at room temperature and then heated at 80° C. for 1 h. The reaction was cooled to room temperature, poured carefully over saturated aqueous sodium bicarbonate solution (200 mL), and the aqueous layer was made basic to pH˜8 by the addition of solid sodium bicarbonate. The solution was extracted with ethyl acetate (200 mL) and the organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (0-60% EtOAc/hexanes) to afford 13-1 as an oil. MS: m/z=504.4 (M+H).

Workup

  1. temperatureheated at 80° C. for 1 h
  2. temperatureThe reaction was cooled to room temperature
  3. extractionThe solution was extracted with ethyl acetate (200 mL)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-77927ba6493b441cb02f114eef5310be
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428492B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes