Sodium hydride → HCID 10389763, compound

HRID 1173173Notes

Reaction equation

HRID 1173173 reaction equation
[CH:1]1([N:7]2[CH2:11][C@H:10]([OH:12])[C@@H:9]([NH:13][C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:32](Br)[C:33]#[C:34][CH3:35].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH2:32]([O:12][C@H:10]1[CH2:11][N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][C@@H:9]1[NH:13][C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=1)[C:33]#[C:34][CH3:35]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27568621-Bromo-2-butyneHCID 9823020HCID 9823020, compound

Product 1

HCID 10389763HCID 10389763, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound of Example 1 (41 mg, 0.1 mmol) in THF (3 mL) cooled in an ice bath was added NaH (16 mg, 0.4 mmol) followed by 2-butynyl bromide (9.6 μL, 0.11 mmol). After being stirred in the ice bath for 3 hours, saturated NH4Cl was added followed by EtOAc. The EtOAc layer was separated, washed with brine, dried over MgSO4 and concentrated. Purification by reversed phase HPLC gave the title compound as a powder. MS calculated (M+H)+ 466, found 466.

Workup

  1. customThe EtOAc layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by reversed phase HPLC

Sources & evidence

ORD record
ord-f2ba6437804a42b2857499aed4dee2bd
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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