Lithium Hydroxide → HCID 11377725, compound

HRID 983901Notes

Reaction equation

HRID 983901 reaction equation
C([O:3][C:4]([C@@:6]12[CH2:24][C@H:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:14](=[O:33])[N:13]1[C@@H:9]([CH2:10][C@@H:11]([O:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=4)[N:38]=[C:37]([C:47]4[N:48]=[C:49]([NH:52][C:53](=[O:55])[CH3:54])[S:50][CH:51]=4)[CH:36]=3)[CH2:12]1)[C:8](=[O:56])[NH:7]2)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[C:53]([NH:52][C:49]1[S:50][CH:51]=[C:47]([C:37]2[CH:36]=[C:35]([O:34][C@@H:11]3[CH2:10][C@@H:9]4[N:13]([C:14](=[O:33])[C@@H:15]([NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][C@H:23]5[C@:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:56])[CH2:24]5)[CH2:12]3)[C:44]3[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=3)[N:38]=2)[N:48]=1)(=[O:55])[CH3:54]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86759613HCID 86759613, compound

Product 1

HCID 11377725HCID 11377725, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step 29i) Following an analogous experimental and purification procedure to Step 1i, (1S,4R,6S,14S,18R)-7-cis-18-[2-(2-Acetylaminothiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-14-tert-butoxycarbonylamino-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic ethyl ester (180 mg, 0.228 mmol) in 14 mL of THF and 3.5 mL of MeOH was reacted with 92 mg (2.3 mmol) of LiOH in 7 mL of H2O to afford (1S,4R,6S,14S,18R)-7-cis-18-[2-(2-Acetylaminothiazol-4-yl)-7-methoxyquinolin-4-yloxy]-14-tert-butoxycar-bonylamino-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene-4-carboxylic acid (150 mg, 86%): 1H NMR (500 MHz, CD3OD, some minor broadening due to rotomers) δ 11.29 (s, 9H), 1.41 (m, 7H), 1.62 (m, 2H), 1.84 (m, 1H), 1.96 (m, 1H), 2.18 (m, 1H), 2.24 (s, 3H), 2.50 (m, 1H), 2.62 (m, 1H), 2.68 (m, 1H), 3.96 (s, 3H), 4.11 (s, 1H), 4.29 (s, 1H), 4.65 (s, 2H), 5.51 (s, 3H), 7.05 (s, 1H), 7.37 (s, 1H) 7.55 (s, 1H), 7.95 (s, 1H), 8.12 (s, 1H): LC-MS m/e 763 (retention time: 3.09, method D, except gradient time increased from 2 to 4 min). Step 29j: Preparation of Compound 28, Example 29, (1S,4R,6S,14S,18R)-7-cis-{18-[2-(2-Acetylaminothiazol-4-yl)-7-methoxyquinolin-4-yloxy]-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]nonadec-7-en-14-yl}carbamic acid tert-butyl ester

Sources & evidence

ORD record
ord-2b294305324d496387a028267e601cb3
Source dataset
uspto-grants-2005_03
Patent number
US06867185B2

Reaction notes

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