Sodium hydride → HCID 67301495, compound

HRID 643587Notes

Reaction equation

HRID 643587 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C@@H:12]([OH:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=[CH:8][C:9]=1[Cl:10].[O:19]=[C:20]1[N:26]([CH:27]2[CH2:32][CH2:31][N:30]([C:33](Cl)=[O:34])[CH2:29][CH2:28]2)[CH2:25][CH2:24][C:23]2[CH:36]=[CH:37][CH:38]=[CH:39][C:22]=2[NH:21]1>C1COCC1>[O:19]=[C:20]1[N:26]([CH:27]2[CH2:28][CH2:29][N:30]([C:33]([O:18][C@@H:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][C:6]3[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=3)=[O:34])[CH2:31][CH2:32]2)[CH2:25][CH2:24][C:23]2[CH:36]=[CH:37][CH:38]=[CH:39][C:22]=2[NH:21]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67301161HCID 67301161, compoundHCID 86615684HCID 86615684, compound

Product 1

HCID 67301495HCID 67301495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

450 mg (55% in mineral oil, 10.3 mmol) NaH were added batchwise to a solution of 2.6 g (9.9 mmol) ethyl(R)-3-(3,4-dichloro-phenyl)-2-hydroxy-propionate in 50 mL THF cooled to 0° C. and stirred for a further 30 min at this temperature. Subsequently 3.7 g (11.9 mmol) 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonylchloride were added batchwise while being cooled and the reaction mixture was stirred overnight at RT. The reaction solution was evaporated down i.vac., the residue combined with DCM, the organic phase was separated off, washed with 10% citric acid solution and 15% K2CO3 solution and dried over Na2SO4. After the desiccant and solvent had been eliminated the product was obtained which was reacted without any further purification.

Workup

  1. temperaturewhile being cooled
  2. stirringthe reaction mixture was stirred overnight at RT
  3. customThe reaction solution was evaporated down i.vac
  4. customthe organic phase was separated off
  5. washwashed with 10% citric acid solution and 15% K2CO3 solution
  6. dry with materialdried over Na2SO4
  7. customwas obtained which
  8. customwas reacted without any further purification

Sources & evidence

ORD record
ord-3c20486f792746b1bf76045db86df19a
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

Loading…