Lithium Hydroxide → HCID 86591193, compound

HRID 983889Notes

Reaction equation

HRID 983889 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](NC(OC(C)(C)C)=O)[C:14](=[O:32])[N:13]1[C@@H:9]([CH2:10][C@@H:11]([O:33][C:34]3[C:43]4[C:38](=[CH:39][C:40]([O:44][CH3:45])=[CH:41][CH:42]=4)[N:37]=[C:36]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[CH:35]=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@@H:15]1[C:14](=[O:32])[N:13]2[C@:9]([N:7]=[C:8]=[O:52])([CH2:10][C@@H:11]([O:33][C:34]3[C:43]4[C:38](=[CH:39][C:40]([O:44][CH3:45])=[CH:41][CH:42]=4)[N:37]=[C:36]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[CH:35]=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)([CH3:23])([CH3:22])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86591194HCID 86591194, compound

Product 1

HCID 86591193HCID 86591193, compoundYield 201.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Following the experimental and purification procedure of Step 1i, (1S,4R,6S,13S,17R)-7-cis-13-tert-butoxycarbonylamino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo [13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester (290 mg, 0.406 mmol) was reacted with 100 mg (2.5 mmol) of LiOH in 23.9 mL of 14.4:7.7:1.8 of THF/H2O/MeOH to afford (1S,4R,6S,13S,17R)-7-cis-13-tert-butoxy-carbonylamino-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 (279 mg, 100%): 1H NMR (300 MHz, CD3OD) δ 0.97-1.05 (m, 2H), 1.14 (s, 9H), 1.20-1.55 (m, 5H), 1.60-1.73 (m, 2H), 1.85 (brs, 1H), 2.06-2.22 (m, 1H), 2.29 (brs, 1H), 2.52-2.73 (m, 2H), 3.93 (s, 3H), 4.14-4.19 (m, 1H), 4.26 (d, J=9.5 Hz, 1H), 4.56-4.67 (m, 2H), 5.47-5.53 (m, 2H), 5.71-5.78 (m, 1H), 7.08 (dd, J=9.1, 2.2 Hz, 1H), 7.22 (s, 1H), 7.37 (d, J=2.2 Hz, 1H), 7.45-7.56 (m, 3H), 8.02, 8.04 (2s, 2H), 8.09 (d, J=9.1 Hz, 1H). LC-MS (Method E-retention time: 1.60), MS m/z 685 (M++1). Step 7j: Preparation of Compound 7, Example 7 (1S,4R,65,13S,17R)-7-cis-[4-Cyclopropanesulfonylamino-carbonyl-17-(7-methoxy-2-phenylquinolin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octadec-7-en-13-yl]carbamic acid tert-butyl ester

Sources & evidence

ORD record
ord-36e432c45e4f4360b1e4743696bf872b
Source dataset
uspto-grants-2005_03
Patent number
US06867185B2

Reaction notes

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