Tetrahydrofuran → HCID 68579296, compound

HRID 644349Notes

Reaction equation

HRID 644349 reaction equation
[H-].[Na+].N[C@H:4]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[C:18]([CH2:24][CH3:25])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[O:26]=[C:27]1[N:33]([CH:34]2[CH2:39][CH2:38][N:37]([C:40](Cl)=[O:41])[CH2:36][CH2:35]2)[CH2:32][CH2:31][C:30]2[CH:43]=[CH:44][CH:45]=[CH:46][C:29]=2[NH:28]1.C1C[O:50]CC1>>[O:26]=[C:27]1[N:33]([CH:34]2[CH2:39][CH2:38][N:37]([C:40]([O:50][C@@H:4]([C:5]([O:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:6])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[C:18]([CH2:24][CH3:25])[CH:17]=3)=[O:41])[CH2:36][CH2:35]2)[CH2:32][CH2:31][C:30]2[CH:43]=[CH:44][CH:45]=[CH:46][C:29]=2[NH:28]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 69712852HCID 69712852, compoundHCID 86615684HCID 86615684, compound

Product 1

HCID 68579296HCID 68579296, compound

Procedure

87 mg (2.0 mmol) sodium hydride (55% in mineral oil) were added to an ice-cooled mixture of 600 mg (1.9 mmol) benzyl (R)-2-amino-3-(3,4-diethyl-phenyl)-propionate and 40 mL THF, stirred for 30 min at RT, cooled in the ice bath and 660 mg (2.1 mmol) 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonylchloride in 20 mL THF were added dropwise within 10 min. The reaction mixture was stirred for a further 30 min while cooling with ice and for 1 h at RT and then evaporated down under reduced pressure. The residue was taken up in EtOAc and purified by chromatography on silica gel.

Workup

  1. temperaturecooled
  2. additionwere added dropwise within 10 min
  3. stirringThe reaction mixture was stirred for a further 30 min
  4. temperaturewhile cooling with ice and for 1 h at RT
  5. customevaporated down under reduced pressure
  6. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-f7167360dde440618651735e137e4791
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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