4-Methylmorpholine → HCID 86756857, compound

HRID 1978816Notes

Reaction equation

HRID 1978816 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C@H:18]([CH2:23][OH:24])[CH2:19][CH:20]([CH3:22])[CH3:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>C(#N)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([NH:17][C@H:18]([CH2:23][OH:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])[C:10]([CH3:11])([CH3:12])[CH3:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 111307L-LeucinolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 86756857HCID 86756857, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of N-tert-butyloxycarbonyl-L-tert-butylglycine 8 (2.43 g, 10.5 mmol), L-leucinol 9 (1.23 g, 10.5 mmol) and TBTU (3.44 g, 11.5 mmol) in acetonitrile (30 mL) at 0° (ice bath) was added N-methyl morpholine (1.3 mL, 11.5 mmol). The resulting mixture was stirred 19 h (allowing the ice bath to warm to room temperature) and the white solid was collected on a filter (486 mg, 14% yield). The mother liquors were purified by flash chromatography (SiO2, 25-35% EtOAc-hexane) affording N-tert-butyloxycarbonyl-L-tert-butylglycyl-L-leucinol 10 (2.79 g, 80% yield) as a white solid (including the filtered solid).

Workup

  1. customwas collected on
  2. filtrationa filter (486 mg, 14% yield)
  3. customThe mother liquors were purified by flash chromatography (SiO2, 25-35% EtOAc-hexane)

Sources & evidence

ORD record
ord-10d1169fead94d749fb34913eee59801
Source dataset
uspto-grants-2001_05
Patent number
US06239125B1

Reaction notes

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