Trifluoromethanesulfonate → HCID 53983472, compound

HRID 271856Notes

Reaction equation

HRID 271856 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C@](N=C=O)(CC1C=CC(O)=CC=1)C(OC)=O)(C)(C)C.[O-]S(C(F)(F)F)(=O)=O>>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][S:23]([C:26]([F:29])([F:27])[F:28])(=[O:25])=[O:24])=[CH:20][CH:21]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 2758875TrifluoromethanesulfonateHCID 10789275(S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoateHCID 86601622methyl (R)-2-tert-butoxy-carbonylamino-3-(4-hydroxyphenyl)propionate

Product 1

HCID 53983472HCID 53983472, compoundYield 91%

Procedure

In a manner similar to the preparation of ethyl (S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl)propionate (Example 1b), using 25 g (84.7 mmol) of methyl (R)-2-tert-butoxy-carbonylamino-3-(4-hydroxyphenyl)propionate, 33 g of triflate are isolated with a 91% yield.

Workup

  1. customare isolated with a 91% yield

Sources & evidence

ORD record
ord-f6b7d6c8eebc469eb6d9b4892661da2c
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

Loading…