Dichloromethane → Boc-Thr(Bzl)-Phe-OEt

HRID 443729

Reaction equation

HRID 443729 reaction equation
C(Cl)Cl.[NH:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:5]([C:16]([OH:18])=O)[C@@H:6]([CH3:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:26][C@H:27]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl.CCN=C=NCCCN(C)C>C(OCC)(=O)C>[NH:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:5]([C:16]([NH:26][C@H:27]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:18])[C@@H:6]([CH3:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 1549483L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 131712163Boc-Thr(Bzl)-Phe-OEtYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 200 ml of methylene chloride, were added 31.0 g of Boc-Thr(Bzl)-OH and 27.6 g of Phe-OEt.HCl, and 18.3 ml of WSC were added to the mixture under cooling at 0°--5° C., which was then subjected to stirring for 2 hours at 0°--5° C. then for 18 hours at room temperature. The methylene chloride in the reaction solution was exchanged with ethyl acetate and the exchanged solution was washed successively with 1 N HCl, 5% aqueous NaHCO3 solution and water and dried over MgSO4. The organic layer was concentrated and the produced material was crystallized from hexane, which gave 39.0 g (yield=81%) of the title compound. m.p. 99°-100.5° C. [α]D25 +6.2° (C 2.7, DMF). Analysis--Calculated for C27H36O6N2 : C, 66.92; H, 7.49; N, 5.78. Found: C, 66.91; H, 7.57; N, 5.75.

Workup

  1. additionwere added to the mixture
  2. temperatureunder cooling at 0°--5° C.
  3. waitfor 18 hours at room temperature
  4. washthe exchanged solution was washed successively with 1 N HCl, 5% aqueous NaHCO3 solution and water
  5. dry with materialdried over MgSO4
  6. concentrationThe organic layer was concentrated
  7. customthe produced material was crystallized from hexane, which

Sources & evidence

ORD record
ord-a7d1204e4ef04932a9986867138df29c
Source dataset
uspto-grants-1981_04
Patent number
US04261885

Linked notes

Loading…