(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid → 7-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]-8-[2-(dimethylamino)-2-oxoethyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine
Reaction equation
Cl.[CH3:2][N:3]([CH3:20])[C:4](=[O:19])[CH2:5][CH:6]1[NH:11][CH2:10][CH2:9][N:8]2[N:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=[C:7]12.[C:21]([O:25][C:26]([NH:28][C@H:29]([CH2:34][C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[CH:37][C:36]=1[F:43])[CH2:30][C:31](O)=[O:32])=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([NH:28][C@H:29]([CH2:34][C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[CH:37][C:36]=1[F:43])[CH2:30][C:31]([N:11]1[CH2:10][CH2:9][N:8]2[N:12]=[C:13]([C:15]([F:17])([F:16])[F:18])[N:14]=[C:7]2[CH:6]1[CH2:5][C:4]([N:3]([CH3:2])[CH3:20])=[O:19])=[O:32])=[O:27])([CH3:24])([CH3:22])[CH3:23]Participants
3
Reactant 2
Product 1
Procedure
A 200 mg portion of 8-[2-(dimethylamino)-2-oxoethyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine, hydrochloride was coupled to (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid essentially following the procedure outlined in Example 2, Step D. Purification by preparative TLC (silica gel, 10% methanol/dichloromethane) followed by HPLC (AD chiral pak column, 15% isopropanol/heptane) separated the first and last eluting diastereomers. LC/MS 593 (M+1).
Workup
- customPurification by preparative TLC (silica gel, 10% methanol/dichloromethane)
- customseparated the first and
- washlast eluting diastereomers
Sources & evidence
- ORD record
- ord-257bbce83d9b49d2a05dc66f127914b4
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390809B2
Reaction notes
Loading…