4-Nitrophenyl formate → tert-Butyl {2-(formylamino)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 2402771Notes

Reaction equation

[NH2:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.[CH:22](OC1C=CC([N+]([O-])=O)=CC=1)=[O:23]>C1COCC1>[CH:22]([NH:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Of the compound from Example 22A, 75 mg (0.25 mmol) were introduced in 1.5 ml of THF and admixed at 0° C. in small portions with 43.25 mg (0.26 mmol) of 4-nitrophenyl formate. The mixture was stirred at 0° C. for 2 h and then at RT overnight. The solvent was removed on a rotary evaporator and the residue was taken up in DMSO and purified by preparative HPLC (method 10). This gave 66 mg (81% of theory) of the title compound.

Workup

customat RT
customovernight
customThe solvent was removed on a rotary evaporator
custompurified by preparative HPLC (method 10)

Sources & evidence

ORD record: ord-38220d24fa44474daa612ab8b4af353d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796324B2

Reaction notes

Loading…