4-(3-(Benzofurazan-4-yl)propyl)piperidine → 2-(R)-(3-(S)-((4-(3-(Benzofurazan-4-yl)propyl)piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-2-(cyclohexyl)acetic acid
Reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][N:5]([CH:15]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:16]([O:18]CC2C=CC=CC=2)=[O:17])[CH2:4]1)=O.[N:32]1[O:36][N:35]=[C:34]2[C:37]([CH2:41][CH2:42][CH2:43][CH:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)=[CH:38][CH:39]=[CH:40][C:33]=12>>[N:32]1[O:36][N:35]=[C:34]2[C:37]([CH2:41][CH2:42][CH2:43][CH:44]3[CH2:49][CH2:48][N:47]([CH2:1][C@@H:3]4[C@@H:7]([C:8]5[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=5)[CH2:6][N:5]([C@H:15]([CH:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)[C:16]([OH:18])=[O:17])[CH2:4]4)[CH2:46][CH2:45]3)=[CH:38][CH:39]=[CH:40][C:33]=12Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 30 mg (0.071 mmol) 2-(R)-((3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 102, Step A) and 4-(3-(benzofurazan-4-yl)propyl)piperidine. HCl (from EXAMPLE 117, Step B) using procedures analogous to those described in EXAMPLE 1, Steps J and K. For the title compound: HPLC (Zorbax SB-C8 4.6 mm×7.5 cm column, gradient elution using 10:90 v/v CH3CN/H2O+0.1% TFA to 100% CH3CN over 7.5 min, hold for 45 sec, 2.25 mL/min, 220 nm): Retention Time: 4.31 min; ESI-MS 563.0 (M+H).
Workup
- washFor the title compound: HPLC (Zorbax SB-C8 4.6 mm×7.5 cm column, gradient elution using 10:90 v/v CH3CN/H2O+0.1% TFA to 100% CH3CN over 7.5 min, hold for 45 sec, 2.25 mL/min, 220 nm)
Sources & evidence
- ORD record
- ord-5852c569585a4329950e9335889465d1
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265434B1
Reaction notes
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