4-Methylmorpholine → HCID 67774386, compound

HRID 1808772Notes

Reaction equation

HRID 1808772 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C[N:39]1[CH2:44][CH2:43][O:42]C[CH2:40]1.Cl.N1CC(O)C1>C(Cl)Cl.CN(C=O)C>[OH:42][CH:43]1[CH2:44][N:39]([C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:13]([CH3:15])[CH3:14])[CH2:40]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 83693Boc-L-ValineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 67774386HCID 67774386, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-(Tert-butoxycarbonylamino)-3-methylbutanoic acid (30.00 g, 138.08 mmol), which is commercially available, and TBTU (48.8 g, 151.9 mmol) was mixed in DCM (400 mL). The mixture was cooled to 0° C. and NMM (45.5 mL, 414.2 mmol) and DMF (100 mL) was added. After 30 min at rt was azetidin-3-ol hydrochloride (18.15 g, 165.7 mmol) added. The resultant mixture was stirred at rt over night. The mixture was washed with NaHCO3 (saturated, 2×300 mL) and brine (300 mL), filtered through a phase separator and concentrated under reduced pressure to give the title compound (35 g, 93%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CD3OD) δ 0.74-1.10, 1.45, 1.67-2.14, 3.58-3.91, 3.92-4.34, 4.37-4.52, 4.52-4.72. Total no of protons: 23. LCMS (M+H)+: 273.

Workup

  1. washThe mixture was washed with NaHCO3 (saturated, 2×300 mL) and brine (300 mL)
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ec9f0fb4ba64017a10397927c2ea33c
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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