1-Phenethylamine → HCID 86749880, compound

HRID 864097Notes

Reaction equation

HRID 864097 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[C@H:10]([CH3:12])[OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.ON1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.Cl.CN(C)CCCCCN=C=N.[CH3:39][CH:40]([NH2:47])[C:41]1C=CC=CC=1.CN1CCOCC1.[Cl-].[Na+].O.O>CN(C)C=O>[CH3:7][C:4]([CH3:5])([O:3][C:1]([NH:8][C@@H:9]([C:13]([NH:47][CH:40]([CH3:41])[CH2:39][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:15])[C@H:10]([CH3:12])[OH:11])=[O:2])[CH3:6]

Participants

8

Reactant 6

HCID 74081-PhenethylamineHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 6992538(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanoic acidHCID 23713072Sodium chloride dihydrateHCID 574828161-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride

Product 1

HCID 86749880HCID 86749880, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-Boc-L-allothreonine (0.325 g, 1.48 mmol, 1.00 eq.) and 1-hydroxybenzotriazole hydrate (0.221 g, 1.64 mmol, 1.11 eq.) in dimethylformamide (5 mL) at 0° C. was added 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (WSC) (0.312 g, 1.63 mmol, 1.10 eq.). After 0.5 hr, a solution of (R) α-methylbenzylamine (0.20 mL, 1.55 mmol, 1.05 eq.) in dimethylformamide (3 mL) was added, followed by 4-methylmorpholine (0.16 mL, 1.46 mmol, 0.98 eq.). After 17 hr, the reaction mixture was poured into a brine/water solution (1:1) and extracted twice with ethyl acetate. The organic layers were combined and washed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate, water, dried over sodium sulfate, and the organic layer concentrated in vacuo to give title compound (0.448 g, 93.9%):

Workup

  1. waitAfter 17 hr
  2. extractionextracted twice with ethyl acetate
  3. washwashed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate, water
  4. dry with materialdried over sodium sulfate
  5. concentrationthe organic layer concentrated in vacuo

Sources & evidence

ORD record
ord-2e881179245d4df1b236c32befc74f36
Source dataset
uspto-grants-1996_10
Patent number
US05561146

Reaction notes

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