4-Methylmorpholine → HCID 22402464, compound

HRID 260128Notes

Reaction equation

HRID 260128 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]2[CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:28](O)=[O:29])=[CH:24][CH:25]=3)[C:20]2=[O:31])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32]([O:34][C:35](=[O:39])[CH2:36][CH2:37][NH2:38])[CH3:33].Cl.CN1CCOCC1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CC#N.CCOC(C)=O>[CH2:32]([O:34][C:35](=[O:39])[CH2:36][CH2:37][NH:38][C:28]([C:23]1[CH:22]=[C:21]2[C:26]([CH2:27][CH:19]([CH2:18][CH2:17][CH:14]3[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:16][CH2:15]3)[C:20]2=[O:31])=[CH:25][CH:24]=1)=[O:29])[CH3:33]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 22402465HCID 22402465, compound

Product 1

HCID 22402464HCID 22402464, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 1-4 (0.45 g, 1.2 mmol), β-alanine ethyl ester·HCl (Aldrich) (0.184 g, 1.2 mmol), in CH3CN (2 mL) was treated with N-methylmorpholine (0.4 mL, 3.6 mmol) and BOP reagent (0.8 g, 1.8 mmol) and stirred at room temperature for 24 h. The solution was diluted with EtOAc, washed with H2O, 10% KHSO4 and brine, dried (MgSO4), filtered, concentrated and chromatographed (30% EtOAc/Hexanes) to give 1-5 as a tan solid. Rf (30% EtOAc/Hexanes) 0.22 1H NMR (300 MHz, CDCl3) δ 8.14 (d, 1H), 8.03 (s, 1H), 7.59 (d, 1H), 7.3 (m, 5H), 6.92 (m, 1H), 5.12 (s, 2H), 4.2-4.1 (m, 4H), 3.75 (dd, 2H), 3.4 (m, 1H), 2.92 (dd, 1H), 2.78 (m, 2H), 2.17 (t, 2H), 2.41 (dd, 1H), 2.0 (m, 1H), 1.7 (m, 3H), 1.6- 11 (m, 6H), 1.3 (t, 3H).

Workup

  1. washwashed with H2O, 10% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6b0c69b512ad409db78489388e5334f6
Source dataset
uspto-grants-1996_06
Patent number
US05525617

Reaction notes

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