Acetate → HCID 86684206, compound

HRID 1411534Notes

Reaction equation

HRID 1411534 reaction equation
C([O-])(=O)C.C([O:8][CH2:9][C:10]1[C:11]([N:42]2[CH2:54][CH2:53][N:45]3[C:46]4[CH2:47][CH2:48][CH2:49][CH2:50][C:51]=4[CH:52]=[C:44]3[C:43]2=[O:55])=[N:12][CH:13]=[CH:14][C:15]=1[C:16]1[CH:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][N:32]([CH:35]4[CH2:38][O:37][CH2:36]4)[CH2:31][C@@H:30]3[CH3:39])=[CH:25][N:24]=2)[C:19](=[O:40])[N:18]([CH3:41])[CH:17]=1)(=O)C.O[Li].O>CC(O)C.C1COCC1.O>[OH:8][CH2:9][C:10]1[C:11]([N:42]2[CH2:54][CH2:53][N:45]3[C:46]4[CH2:47][CH2:48][CH2:49][CH2:50][C:51]=4[CH:52]=[C:44]3[C:43]2=[O:55])=[N:12][CH:13]=[CH:14][C:15]=1[C:16]1[CH:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][N:32]([CH:35]4[CH2:38][O:37][CH2:36]4)[CH2:31][C@@H:30]3[CH3:39])=[CH:25][N:24]=2)[C:19](=[O:40])[N:18]([CH3:41])[CH:17]=1

Participants

6

Reactant 3

HCID 175AcetateHCID 168937Lithium hydroxide, monohydrateHCID 86684207HCID 86684207, compound

Product 1

HCID 86684206HCID 86684206, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

Following the procedures as described for 118, acetate hydrolysis of 119a with LiOH.H2O in iPrOH/THF (1:1) and H2O, gave 119 as a white solid (184 mg, 85%). LCMS: [M+H]+ 651. 1H NMR (500 MHz, CDCl3) δ 8.65 (d, J=2.5, 1H), 8.50 (d, J=5.0, 1H), 7.99 (s, 1H), 7.87 (s, 1H), 7.84 (d, J=2.0, 1H), 7.35 (d, J=5.0, 1H), 7.33 (d, J=7.0, 1H), 6.90 (s, 1H), 6.83 (d, J=9.0, 1H), 5.04-5.06 (m, 1H), 4.62-4.73 (m, 5H), 4.51 (s, 1H), 4.32 (s, 1H), 4.16 (s, 1H), 4.11 (s, 1H), 3.89 (s, 1H), 3.72 (s, 3H), 3.57 (t, J=6.0, 1H), 3.48 (s, 1H), 3.07-3.12 (m, 2H), 2.53-2.63 (m, 7H), 2.24 (m, 1H), 1.88-1.93 (m, 2H), 1.80 (s, 2H), 0.99 (d, J=6.5, 3H).

Sources & evidence

ORD record
ord-b78fc36f5eb94767a036ecb819729462
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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