Benzyl Bromide → Rel-n-(2-{[(3r,4r)-4-(benzyloxy)-1-(tetrahydro-2h-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

HRID 564411Notes

Reaction equation

[CH2:1]([O:4][C@@H:5]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:7][C@H:6]1[NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)[CH:2]=[CH2:3].[CH2:33](Br)[C:34]1C=CC=[CH:36][CH:35]=1.C(Br)C=C>>[CH2:1]([O:4][C@@H:5]1[CH2:9][N:8]([CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH2:7][C@H:6]1[NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=1)[C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:3]=1

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 7841Allyl bromide

HCID 67005152Rel-n-(2-{[(3r,4r)-4-(allyloxy)-1-(tetrahydro-2h-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 57814106Rel-n-(2-{[(3r,4r)-4-(benzyloxy)-1-(tetrahydro-2h-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

Procedure

The title compound was synthesized in similar fashion to rel-N-(2-{[(3R,4R)-4-(allyloxy)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide, benzyl bromide was substituted for allyl bromide and was isolated as a white solid. 1H-NMR (MeOD) δ: 1.51 (m, 2H), 1.82 (m, 2H), 2.40 (m, 1H), 2.58 (m, 1H), 2.76 (m, 1H), 3.02-3.14 (m, 2H), 3.40 (m, 2H), 3.91-3.98 (m, 3H), 4.05 (s, 2H), 4.41 (m, 1H), 4.60 (m, 2H), 7.26-7.38 (m, 5H), 7.70 (t, J=7.7 Hz, 1H), 7.87 (d, J=7.7 Hz, 1H), 8.15 (d, J=7.7 Hz, 1H), 8.23 (s, 1H) MS m/z: 506 (M+1).

Workup

customwas isolated as a white solid

Sources & evidence

ORD record: ord-1e7069cbf23945c6a5cef66a3b821d01
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067457B2

Reaction notes

Loading…