Lithium Hydroxide → HCID 86591191, compound

HRID 983888Notes

Reaction equation

HRID 983888 reaction equation
C([O:3][C:4]([C@@:6]12[CH2:23][C@H:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][C@H:15](C(OC(C)(C)C)=O)[C:14](=[O:31])[N:13]1[C@@:9](N)([CH2:10][C@@H:11]([O:32][C:33]3[C:42]4[C:37](=[CH:38][C:39]([O:43][CH3:44])=[CH:40][CH:41]=4)[N:36]=[C:35]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH:34]=3)[CH2:12]1)[C:8](=[O:52])[NH:7]2)=[O:5])C.[Li+].[OH-:54]>C1COCC1.O.CO>[C:6]([O:54][C:14]([NH:13][C@@H:15]1[C:14](=[O:31])[N:13]2[C@@H:9]([CH2:10][C@@H:11]([O:32][C:33]3[C:42]4[C:37](=[CH:38][C:39]([O:43][CH3:44])=[CH:40][CH:41]=4)[N:36]=[C:35]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH:34]=3)[CH2:12]2)[C:8](=[O:52])[NH:7][C@@:6]2([C:4]([OH:3])=[O:5])[C@@H:22]([CH2:23]2)[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:31])([CH3:23])([CH3:22])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86591192HCID 86591192, compound

Product 1

HCID 86591191HCID 86591191, compoundYield 198.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Following the experimental and purification procedure of Step 2i, (1S,4R,6S,13S,17R)-7-trans-13-tert-butoxycarbonyl-amino-17-(7-methoxy-2-phenylquin-olin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester (185 mg, 0.265 mmol) was reacted with 64 mg (1.6 mmol) of LiOH in 15.5 mL of 9:5:1.5 of THF/H2O/MeOH to afford (1S,4R,6S,13S,17R)-7-trans-13-tert-butoxycar-bonylamino-17-(7-methoxy-2-phenylquinolin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid (180 mg, 100%): 1H NMR (300 MHz, CD3OD) δ 1.14 (s, 9H), 1.20-1.51 (m, 5H), 1.53-1.58 (m, 1H), 1.70 (dd, J=9.9, 5.1 Hz, 1H), 1.86 (brs, 1H), 2.06 (brs, 1H), 2.28-2.59 (m, 3H), 2.65-2.73 (m, 1H), 3.94 (s, 3H), 4.07 (dd, J=11.3, 2.6 Hz, 1H), 4.23 (d, J=8.4 Hz, 1H), 4.64-4.70 (m, 2H), 5.54-5.68 (m, 3H), 7.10 (dd, J=9, 2 Hz, 1H), 7.26 (s, 1H), 7.39 (d, J=2.2 Hz, 1H), 8.02, 8.04 (2s, 2H), 8.12 (d, J=9.1 Hz, 1H). LC-MS (Method E-retention time: 1.57), MS m/z 685 (M++1). HRMS m/z (M+H)+ calcd for C38H45N4O8: 685.3238, found 685.3241. Step 5j: Preparation of Compound 5, Example 5 (1S,4R,6S,13S,17R)-7-trans-[4-Cyclopropanesul-fonylamino-carbonyl-17-(7-methoxy-2-phenylquinolin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octa-dec-7-en-13-yl]carbamic acid tert-butyl ester

Sources & evidence

ORD record
ord-d84e00d6f20545c1a34e97908fb6fe97
Source dataset
uspto-grants-2005_03
Patent number
US06867185B2

Reaction notes

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