Sodium hydride → HCID 86666933, compound

HRID 511014Notes

Reaction equation

HRID 511014 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH:8]([C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH3:17])=[C:12]([CH:18]([OH:28])[CH2:19][N:20]([C:24](=[O:27])[CH2:25]Cl)[CH:21]([CH3:23])[CH3:22])[C:11]=1[O:29][CH3:30])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>C1COCC1>[Cl:16][C:14]1[C:13]([CH3:17])=[C:12]([CH:18]2[O:28][CH2:25][C:24](=[O:27])[N:20]([CH:21]([CH3:22])[CH3:23])[CH2:19]2)[C:11]([O:29][CH3:30])=[C:10]([CH:8]([NH:7][C:6](=[O:31])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH3:9])[CH:15]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 131733268HCID 131733268, compound

Product 1

HCID 86666933HCID 86666933, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl[1-(5-chloro-3-{2-[(chloroacetyl)(isopropyl)amino]-1-hydroxyethyl}-2-methoxy-4-methylphenyl)ethyl]carbamate (22 mg, 0.047 mmol) in THF (1.0 mL) cooled at 0° C., sodium hydride (3.6 mg, 0.094 mmol; 60% dispersion in mineral oil) was added and the mixture was stirred for 1 hour. The mixture was quenched with water and extracted with EtOAc. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated to give the desired compound (20 mg, 97%). LCMS calculated for C22H33ClN2O5Na (M+Na)+: m/z=463.2. found: 463.1.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-43679fa005254fafb8cbbdfd609d650d
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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