HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Diisopropylethylamine → 3-{[2-[2,6-Bis(isopropyl)phenoxycarbonyl]-benzoyl]amino}-propanoic Acid

HRID 1766138
Notes
Print preview

Reaction equation

HRID 1766138 reaction equation
[CH:1]([C:4]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[C:5]=1[O:6][C:7]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])=[O:8])([CH3:3])[CH3:2].Cl.C([O:30][C:31](=[O:35])[CH2:32][CH2:33][NH2:34])(C)(C)C.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[CH:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[O:6][C:7]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:34][CH2:33][CH2:32][C:31]([OH:35])=[O:30])=[O:12])=[O:8])([CH3:24])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 211100142-[2,6-Bis(isopropyl)phenoxycarbonyl]-benzoic Acid

Product 1

HCID 11418078
3-{[2-[2,6-Bis(isopropyl)phenoxycarbonyl]-benzoyl]amino}-propanoic Acid
Yield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing (102) (2.1 g, 6.4 mmol) and beta-alanine tert-butyl ester hydrochloride (1.16 g, 6.4 mmol) in DMF (20 mL) was added diisopropylethylamine (2.4 mL, 13.7 mmol) followed by O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (2.5 g, 6.5 mmol). The resulting reaction mixture was stirred at room temperature for 14 h, diluted with ethyl acetate (100 mL), washed with 10% aqueous citric acid solution (50 mL), followed by saturated aqueous NaHCO3 solution (50 mL) and brine (2×50 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The crude residue was dissolved in anhydrous dichloromethane (30 mL) and cooled to 0° C. before a solution of hydrochloric acid (10 mL, 4 N in dioxane) was added. The reaction was stirred for 1 h at 0° C. and 1 h at room temperature. The solvent was removed in vacuo and the crude residue was purified by preparative LC/MS to afford 0.85 g (38% yield over three steps) of the title compound (101). 1H NMR (400 MHz, CD3OD): δ 8.20 (dd, J=7.6, 0.8 Hz, 1H), 7.70–7.68 (m, 1H), 7.63–7.59 (m, 1H), 7.49 (dd, J=7.6, 0.8 Hz, 1H), 7.22–7.17 (m, 3H), 3.54 (t, J=7.2 Hz, 2H), 3.06–3.00 (m, 2H), 2.57 (t, J=6.8 Hz, 2H), 1.19 (d, J=6.8 Hz, 12H). MS (ESI) m/z 398.3 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 10% aqueous citric acid solution (50 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved in anhydrous dichloromethane (30 mL)
  6. temperaturecooled to 0° C. before a solution of hydrochloric acid (10 mL, 4 N in dioxane)
  7. additionwas added
  8. stirringThe reaction was stirred for 1 h at 0° C. and 1 h at room temperature
  9. customThe solvent was removed in vacuo
  10. customthe crude residue was purified by preparative LC/MS

Sources & evidence

ORD record
ord-0730ea59c6e94b27bd7fff983dfbe4b5
Source dataset
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07230003B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes