4-Methylmorpholine → HCID 67774387, compound

HRID 1808774Notes

Reaction equation

HRID 1808774 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.CN1CCOCC1.Cl.[CH3:46][C:47]1([OH:51])[CH2:50][NH:49][CH2:48]1>CN(C=O)C>[OH:51][C:47]1([CH3:46])[CH2:50][N:49]([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])[CH2:48]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 83693Boc-L-ValineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 115427813-methylazetidin-3-ol Hydrochloride

Product 1

HCID 67774387HCID 67774387, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-(Tert-butoxycarbonylamino)-3-methylbutanoic acid (5.30 g, 24.4 mmol), and TBTU (9.40 g, 29.3 mmol) was mixed in DMF (50 mL). To the mixture was NMM (6.70 mL, 60.99 mmol) added. After 30 min at rt was 3-methylazetidin-3-ol hydrochloride (3.01 g, 24.39 mmol) added. The resultant mixture was stirred at rt over night. The mixture was concentrated and the residue dissolved in DCM (200 mL). The organic phase was washed with NaHCO3 (saturated, 2×150 mL) and brine (150 mL), filtered through a phase separator and concentrated under reduced pressure to give the title compound (7.00 g, quant. yield). The obtained crude product was used without further purification. 1H NMR (400 MHz, CD3OD) δ 0.76-1.07, 1.31-1.56, 1.78-2.04, 2.55-2.73, 3.64-3.98, 4.04-4.42, 6.52-6.84.

Workup

  1. additionadded
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in DCM (200 mL)
  4. washThe organic phase was washed with NaHCO3 (saturated, 2×150 mL) and brine (150 mL)
  5. filtrationfiltered through a phase separator
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32907ef3df304f49b1a33cc8f31fad1e
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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