2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 59718708, compound

HRID 2219025Notes

Reaction equation

[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]1[CH2:14][N:13]([CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]2[CH:25]=[CH:26][CH:27]=[CH:28][C:11]=2[NH:10][C:9]1=[O:29])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S(O[CH2:37][C:38]([F:41])([F:40])[F:39])(=O)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]1[C:9](=[O:29])[N:10]([CH2:37][C:38]([F:41])([F:40])[F:39])[C:11]2[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=2[N:13]([CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

HCID 2733832Lithium Hexamethyldisilazide

HCID 59718700HCID 59718700, compound

Product 1

HCID 59718708HCID 59718708, compoundYield 86%

Procedure

In an analogous manner to that described in Example 2a), the alkylation of the [(S)-1-(2-benzyloxy-ethyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester with 2,2,2-trifluoroethyl trifluoromethanesulphonate using lithium bis(trimethylsilyl)amide (1M solution in tetrahydrofurane) as the base yielded title compound as a white foam (yield 86% of theory); MS (m/e): 494 (M+H)+.

Sources & evidence

ORD record: ord-bb2d87498122441a9adc3181b8e48991
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414049B2

Reaction notes

Loading…