Triethylamine → HCID 13385132, compound

HRID 462929Notes

Reaction equation

HRID 462929 reaction equation
[NH:1]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C@H:2]([C:18]([O:20]N1C(=O)CCC1=O)=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[NH2:38][C@H:39]([C:42]([O:44][CH3:45])=[O:43])[CH2:40][OH:41].Cl.C(N(CC)CC)C>O1CCCC1.CN(C=O)C>[NH:1]([C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[C@H:2]([C:18]([NH:38][C@H:39]([C:42]([O:44][CH3:45])=[O:43])[CH2:40][OH:41])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 11375677N2,N6-Bis[(phenylmethoxy)carbonyl]-L-lysine 2,5-dioxo-1-pyrrolidinyl ester

Product 1

HCID 13385132HCID 13385132, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Z-Lys(Z)OSu (1.50 g, 2.93 mmole) (see Chladek et al. Collect. Czechr. Chem. Commun. 33: 4299 (1968)) in tetrahydrofuran (15 ml), a solution of H-Ser-OMe-HCl (0.46 g, 2.93 mmole) in N,N'-dimethylformamide (10 ml) containing triethylamine (0.41 ml) was added with stirring at 0° C. The mixture was stirred at 0° C. for 2 hr. and at room temperature for 15 hr. After removal of the solvent, the residue was dissolved in three portions of ethyl acetate, which were washed successively with 1N citric acid, sat. NaHCO3 solution and sat. NaCl solution, and dried over Na2SO4. After evaporating, the residue was solidified by addition of ether and reprecipitated from methanol-ether to yield (IV) (1.19 g, 78.8%). RfI 0.88, RfII 0.86 mp 120°-121° C., [α]D29 -7.8 (C=1.03 methanol)

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at 0° C. for 2 hr
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved in three portions of ethyl acetate, which
  5. washwere washed successively with 1N citric acid, sat. NaHCO3 solution and sat. NaCl solution
  6. dry with materialdried over Na2SO4
  7. customAfter evaporating
  8. additionthe residue was solidified by addition of ether
  9. customreprecipitated from methanol-ether

Sources & evidence

ORD record
ord-d0d84fd4f3d946889aa9ebfb485edd18
Source dataset
uspto-grants-1985_05
Patent number
US04518527

Reaction notes

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