Lithium Hydroxide → HCID 21700383, compound
Reaction equation
C[O:2][C:3](=[O:42])[CH:4]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]2[CH2:17][CH2:16][N:15]([C:18]3[O:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:14]2)=[CH:8][CH:7]=1.[OH-].[Li+]>>[O:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=[C:18]1[N:15]1[CH2:16][CH2:17][CH:13]([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34](=[O:41])[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:3]([OH:42])=[O:2])=[CH:7][CH:8]=2)[CH2:14]1Participants
3
Procedure
The title compound (115 mg) was prepared from 200 mg (0.36 mmol) of 3-[4-(1-Benzoxazol-2-yl-pyrrolidin-3-yloxy)-phenyl]-2-(2-benzoyl-phenylamino)-propionic acid methyl ester and 18 mg (0.43 mmol, 1.2 equiv.) of lithium hydroxide according to the method of Example 32 followed by purification via silica gel flash column chromatography using DCM/MeOH 90/10 as eluent: low resolution MS (ES) m/e 546.0 (MH−); RP-HPLC (Vydac C-18, 25 cm×4.6 mm; 30-80% CH3CN in H2O with 0.1% TFA buffer; 25 minutes; 1 mL/min); tr=17.92 min (t0=3 min). Daicel Chiral OD-H (4.6×250 mm, 5 m; 0.7 mL/min; inj volume 3 mL, UV 230 nM; 40/60/0.1 IPA/Hexane/TEA; 30 min); tr=6.8 min and 10.0 min.
Workup
- customfollowed by purification via silica gel flash column chromatography
- customRP-HPLC (Vydac C-18, 25 cm×4.6 mm; 30-80% CH3CN in H2O with 0.1% TFA buffer; 25 minutes; 1 mL/min)
- customtr=17.92 min (t0=3 min)
- customDaicel Chiral OD-H (4.6×250 mm, 5 m; 0.7 mL/min; inj volume 3 mL, UV 230 nM; 40/60/0.1 IPA/Hexane/TEA; 30 min)
- customtr=6.8 min and 10.0 min.
Sources & evidence
- ORD record
- ord-7e2d4b98ca90489a994da66600652027
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06294580B1
Reaction notes
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