Lithium Hydroxide → HCID 86591189, compound

HRID 983887Notes

Reaction equation

HRID 983887 reaction equation
C([O:3][C:4]([C@@:6]12[CH2:22][C@H:21]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16][C@H:15](C(OC(C)(C)C)=O)[C:14](=[O:30])[N:13]1[C@@:9](N)([CH2:10][C@@H:11]([O:31][C:32]3[C:41]4[C:36](=[CH:37][C:38]([O:42][CH3:43])=[CH:39][CH:40]=4)[N:35]=[C:34]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:33]=3)[CH2:12]1)[C:8](=[O:51])[NH:7]2)=[O:5])C.[Li+].[OH-:53]>C1COCC1.O.CO>[C:6]([O:53][C:14]([NH:13][C@@H:15]1[C:14](=[O:30])[N:13]2[C@@H:9]([CH2:10][C@@H:11]([O:31][C:32]3[C:41]4[C:36](=[CH:37][C:38]([O:42][CH3:43])=[CH:39][CH:40]=4)[N:35]=[C:34]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:33]=3)[CH2:12]2)[C:8](=[O:51])[NH:7][C@@:6]2([C:4]([OH:3])=[O:5])[C@@H:21]([CH2:22]2)[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1)=[O:30])([CH3:22])([CH3:21])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86591190HCID 86591190, compound

Product 1

HCID 86591189HCID 86591189, compoundYield 202.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Following the experimental and purification procedure of Step 1i, (1S,4R,6S,12S,16R)-7-trans-12-tert-butoxycarbonyl-amino-16-(7-methoxy-2-phenylquinolin-4-yloxy)-2,13-dioxo-3,14-diazatricyclo-[12.3.0.04,6]heptadec-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,12S,16R)-7-trans-12-tert-butoxycar-bonyiamino-16-(7-methoxy-2-phenylquinolin-4-yloxy)-2,13-dioxo-3,14-diazatricyclo[12.3.0.04,6]heptadec-7-ene-4-carboxylic acid (180 mg, 100%): 1H NMR (300 MHz, CD3OD) δ 1.24 (s, 9H), 1.33-1.43 (m, 1H), 1.61-1.97 (m, 6H), 2.10 (brs, 1H), 2.28-2.36 (m, 1H), 2.70 (m, 2H), 3.94 (s, 3H), 4.17 (d, J=10.6 Hz, 1H), 4.28 (d, J=4.8 Hz, 1H), 4.65-4.70 (m, 1H), 5.34 (dd, J=15.7, 5.9 Hz, 2H), 5.53-5.62 (m, 2H), 7.14 (d, J=9 Hz, 1H), 7.32 (s, 1H), 7.39 (s, 1H), 7.56 (m, 3H), 8.01-8.02 (m, 2H), 8.22 (d, J=9.2 Hz, 1H). LC-MS (Method E-retention time: 1.49), MS m/z 671 (M++1). HRMS m/z (M+H)+ calcd for C37H43N4O8: 671.3081, found 671.3080. Step 3j: Preparation of Compound 3, Example 3 (1S,4R,6S,12S,16R)-7-trans-[4-Cyclopropanesulfonyl-aminocarbonyl-16-(7-methoxy-2-phenylquinolin-4-yloxy)-2,13-dioxo-3,14-diazatricyclo[12.3.0.04,6]heptadec-7-en-12-yl]carbamic acid tert-butyl ester

Sources & evidence

ORD record
ord-d090d3d2c93347a6b7298307e0299b00
Source dataset
uspto-grants-2005_03
Patent number
US06867185B2

Reaction notes

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