Lithium Hydroxide → HCID 58717795, compound
Reaction equation
C[O:2][C:3](=[O:52])[C@@H:4]([NH:18][C:19](=[O:51])[C:20]1[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:31]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Li+].[OH-]>C1COCC1.CO>[C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]([CH2:5][C@H:4]([NH:18][C:19](=[O:51])[C:20]2[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:31]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:30]=2)[C:3]([OH:52])=[O:2])=[CH:11][CH:10]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Biphenyl-4-yl-2-(S)-[2-(3,4-bis-benzyloxy-benzyloxy)-5-bromo-benzoylamino]-propionic acid methyl ester (60 mg, 0.079 mmol) was dissolved in 5 mL of THF-MeOH (4-1), cooled to 0° C. and 1.1 equiv of 2 N LiOH added. After 30 minutes, 2.2 additional equiv of 2N LiOH was added and the reaction stirred for 30 minutes. The reaction was worked up according to general procedure C to give 3-biphenyl-4-yl-2-(S)-[2-(3,4-bis-benzyloxy-benzyloxy)-5-bromo-benzoylamino]-propionic acid (47 mg). 1H-NMR(400 MHz, DMSO-d6): 2.83 (m, 1H), 3.13 (m, 1H), 4.67 (m, 1H), 5.02 (s, 2H), 5.06 (s, 2H), 5.17, (m, 2H), 6.92 (m, 1H), 6.96 (m, 1H), 7.13 (d, 2H), 7.18-7.22 (m, 2H), 7.27-7.41 (m, 13H), 7.44 (d, 2H), 7.56 (m, 2H), 7.61 (m, 1H), 7.83 (m, 1H), 8.50 (d, 1H); LC/MS (m/z): 742 (M+1)+.
Sources & evidence
- ORD record
- ord-e6d3220d059242c08edbf89d30ffb9eb
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07459472B2
Reaction notes
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