Lithium Hydroxide → HCID 16086934, compound

HRID 1724119Notes

Reaction equation

HRID 1724119 reaction equation
C[O:2][C:3]([C:5]1[CH:58]=[CH:57][C:8]([CH2:9][N:10]([C:47]2[CH:52]=[CH:51][C:50]([C:53]([O:55]C)=[O:54])=[CH:49][CH:48]=2)[C:11](=[O:46])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:21]=[C:20]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:19]=2)=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].C(C1C=CC(N(C2C=CC(C(O)=O)=CC=2)C(=O)CCCCCOC2C=C(OCCCCCCCCCC)C=C(OCCCCCCCCCC)C=2)=CC=1)(O)=O>C1COCC1>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([C:47]2[CH:48]=[CH:49][C:50]([C:53]([OH:55])=[O:54])=[CH:51][CH:52]=2)[C:11](=[O:46])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[C:20]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:21]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:23]=2)=[CH:57][CH:58]=1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 16086931HCID 16086931, compoundHCID 16086954HCID 16086954, compound

Product 1

HCID 16086934HCID 16086934, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 20b (443 mg, 0.552 mmol) in THF (14 ml) is treated with an aqueous solution of LiOH (0.5 M, 3.31 ml, 1.66 mmol) in accordance with the production of compound 2a. 343 mg (80%) of the desired dicarboxylic acid 2b are obtained as a colorless resin. IR (KBr) 3030, 2890, 2820, 2640, 2520, 1700, 1655, 1575 cm−1; 1H-NMR (CDCl3) δ 8.08 (d, 8.6 Hz, 2H), 8.01 (d, 8.4 Hz, 2H), 7.29 (d, 8.4 Hz, 2H), 7.10 (d, 8.6 Hz, 2H), 6.05 (t, 1.9 Hz, 1H), 6.02 (d, 1.9 Hz, 2H), 5.01 (s, 2H), 3.92-3.83 (m, 6H) 2.16 (t, 7.4 Hz, 2H), 1.80-1.62 (m, 8H), 1.49-1.21 (m, 30H), 0.87 (t, 6.7 Hz, 6H); MS (FD) m/z (%) 774 (M+). Anal. calc. for C47H67NO8: C, 72.93; H, 8.72; N, 1.81. Found C, 72.65; H, 8.77; N, 1.77.

Sources & evidence

ORD record
ord-96654eb7bc5842b1b2070233f4c0c640
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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