Dichloromethane → HCID 178425955, compound

HRID 413454Notes

Reaction equation

HRID 413454 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13](=[O:25])[N:14]([CH2:21][C:22]([OH:24])=O)[C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CN([P+](ON1N=NC2C1=CC=CC=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(OC([N:60]([O:71][CH2:72][CH2:73][NH2:74])[C:61]([NH:63]C(OC(C)(C)C)=O)=[NH:62])=O)(C)(C)C.C(N(CC)CC)C.C(Cl)[Cl:83]>>[ClH:83].[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13](=[O:25])[N:14]([CH2:21][C:22]([NH:74][CH2:73][CH2:72][O:71][NH:60][C:61]([NH2:63])=[NH:62])=[O:24])[C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 221786713-(3-Methylphenylsulfonyl)amino-6-isopropyl-1-(carboxymethyl)-2-pyridinoneHCID 140407450tert-butyl N-(2-aminoethoxy)-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate

Product 1

HCID 178425955HCID 178425955, compoundYield 54%

Procedure

3-(3-Methylphenylsulfonyl)amino-6-isopropyl-1-(carboxymethyl)-2-pyridinone (0.71 g, 1.95 mmol), as prepared in the preceding step, Castro's reagent (BOP, 0.905 g, 2.05 mmol), and [N,N′-di(tert-butoxycarbonyl)] 2-aminoethoxyguanidine (0.710 g, 2.00 mmol), as prepared in step 4 of Example 2, were dissolved in methylene chloride (40 mL) and reacted with triethylamine (0.75 mL, 5.4 mmol) at ambient temperature for 3 days. After concentration in vacuo, the crude product was dissolved in methylene chloride, washed with 10% aqueous citric acid, saturated NaHCO3, and brine, dried over Na2SO4, and filtered. The evaporated filtrate was purified by flash column chromatography (5% methanol in methylene chloride) giving the title compound as a light yellow solid (0.70 g, 54%). 1H NMR (300 MHz, CDCl3) δ9.15 (s, 1H), 8.34 (br t, 1H, J=5.0 Hz), 7.67 (m, 3H), 7.59 (s, 1H), 7.40 (d, 1H, J=7.9 Hz), 7.34 (m, 2H), 6.06 (d, 1H, J=7.9 Hz), 4.86 (s, 2H), 4.09 (m, 2H), 3.58 (dd, 2H, J=8.8 Hz, 5.0 Hz), 2.86 (m, 1H), 2.38 (s, 3H), 1.52 (s, 9H), 1.47 (s, 9H), 1.20 (s, 3H), 1.17 (s, 3H).

Workup

  1. customas prepared in step 4 of Example 2
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe crude product was dissolved in methylene chloride
  4. washwashed with 10% aqueous citric acid, saturated NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe evaporated filtrate was purified by flash column chromatography (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-74bf0644663842c9bdcd2be4db79f162
Source dataset
uspto-grants-2003_05
Patent number
US06566379B1

Reaction notes

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