Water → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

HRID 1281910Notes

Reaction equation

HRID 1281910 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[CH3:16][O:17][C:18](=[O:36])[C@H:19]([CH2:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].N1C=CC=CC=1.O>C(Cl)Cl>[C:24]([O:23][C:21]([NH:20][C@@H:19]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[CH:33][CH:34]=1)[C:18]([O:17][CH3:16])=[O:36])=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 7019130Boc-Tyr-OMe

Product 1

HCID 10455198(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triflic anhydride (5.05 ml, 30 mmol) was added to a mixture of N-BOC tyrosine methyl ester (7.38 g, 25 mmol) and pyridine (10 ml, 125 mmol) in DCM (40 ml) at 0°. After 45 min at 0° water (80 ml) and DCM (100 ml) were added. The organic phase was washed with NaOH aq. (0.5 M, 60 ml), water (60 ml), citric acid (10%, 2×80 ml) and water (60 ml), dried (Na2SO4) and concentrated in vacuo to give the title compound as a yellow oil which solidified on standing (10.6 g). δH (CDCl3) 7.26-7.18 (4H, m), 5.05 (1H, v br d), 4.59 (1H, v br q), 3.70 (3H, s), 3.16 (1H, dd, J 13.7, 5.7 Hz), 3.02 (1H, dd, J 13.8, 6.5 Hz), 1.40 (9H, s); m/z (ES+, 70 V) 450 (M++Na).

Workup

  1. washThe organic phase was washed with NaOH aq. (0.5 M, 60 ml), water (60 ml), citric acid (10%, 2×80 ml) and water (60 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56d58ad8ff8240a48c5e07744b92e94f
Source dataset
uspto-grants-2002_09
Patent number
US06455539B2

Reaction notes

Loading…