Diisopropylamine → HCID 131719307, compound

HRID 977525Notes

Reaction equation

HRID 977525 reaction equation
C1(O[C:8]([NH:10][C@H:11]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])C=CC=CC=1.[CH:26]([NH:29]C(C)C)([CH3:28])[CH3:27]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[NH:29]([CH:26]([CH3:28])[CH3:27])[C@:11]([N:10]=[C:8]=[O:9])([C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[CH2:12][CH:13]([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 7912DiisopropylamineHCID 14420147HCID 14420147, compound

Product 1

HCID 131719307HCID 131719307, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of PhOCO-Leu-OBzl (70 mg, prepared in (1)) in chloroform (2 ml) were added diisopropylamine (575 μl) and TEA (286 μl) at room temperature under argon atmosphere. The mixture was stirred at 55° C. for 17 h and cooled to room temperature. The mixture was diluted with ethyl acetate, washed with 1N-hydrochloric acid, sat. aq. NaHCO3 and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with ethyl acetate/hexane=1/4 for development to give the product (32 mg).

Workup

  1. temperaturecooled to room temperature
  2. washwashed with 1N-hydrochloric acid, sat. aq. NaHCO3 and brine successively
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with ethyl acetate/hexane=1/4 for development

Sources & evidence

ORD record
ord-71a7f8dfc7ae497e94d448bbd4d100dc
Source dataset
uspto-grants-1997_03
Patent number
US05614498

Reaction notes

Loading…