Diethyl Ether → HCID 70059617, compound

HRID 2230292Notes

Reaction equation

HRID 2230292 reaction equation
[C:1]([NH:8][C@H:9]([C:27](O)=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:54]([NH2:58])([CH3:57])([CH3:56])[CH3:55].CCOCC>CN(C=O)C.CCN(C(C)C)C(C)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([C:27](=[O:28])[NH:58][C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])=[CH:13][CH:12]=1)([CH3:6])([CH3:5])[CH3:7]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6385Tert-ButylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11133964L-Tyrosine, O-[(2,6-dichlorophenyl)methyl]-N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 70059617HCID 70059617, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of BOC-O-(2,6-dichlorobenzyl)-L-tyrosine (Bachem, 2.00 g, 4.54 mmol) in 20 mL of DMF and iPr2NEt (1.6 mL) was cooled to 0° C. and treated with HBTU (1.72 g, 4.54 mmol). The resulting solution was stirred at 0° C. for 30 minutes and treated with tert-butyl amine (0.48 mL, 4.54 mmol). The resulting solution was stirred overnight. The reaction mixture was poured into ether (100 mL) and washed sequentially with saturated aqueous NaHCO3 solution (20 mL) and brine (4×20 mL). The organic phase was collected and dried (MgSO4) and concentrated. The crude reaction product was purified by chromatography (silica gel, 2:1 heptane/EtOAc). The solid obtained was crystallized from hot heptane, collected by suction filtration and dried to give the title compound as a white solid (1.56 g, 69%), mp=82-86° C.

Workup

  1. stirringThe resulting solution was stirred overnight
  2. washwashed sequentially with saturated aqueous NaHCO3 solution (20 mL) and brine (4×20 mL)
  3. customThe organic phase was collected
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude reaction product
  7. customwas purified by chromatography (silica gel, 2:1 heptane/EtOAc)
  8. customThe solid obtained
  9. customwas crystallized from hot heptane
  10. filtrationcollected by suction filtration
  11. customdried

Sources & evidence

ORD record
ord-e0ea3705da364abbadc5e11464b48aa0
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

Loading…