Water → HCID 85123690, compound

HRID 853710Notes

Reaction equation

HRID 853710 reaction equation
C([O:3][C:4](=[O:45])[CH:5]([O:7][P:8]([CH2:17][CH2:18][NH:19][C:20]([C:22]1[C:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:28]=2[C:29]([OH:44])=[C:30]2[C:34](=[O:35])[N:33]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[CH2:32][C:31]=12)=[O:21])([O:10]C1C=CC=CC=1)=[O:9])[CH3:6])C.O.[OH-].[Na+]>C(#N)C>[F:43][C:40]1[CH:39]=[CH:38][C:37]([CH2:36][N:33]2[C:34](=[O:35])[C:30]3[C:31](=[C:22]([C:20]([NH:19][CH2:18][CH2:17][P:8]([OH:10])([O:7][CH:5]([CH3:6])[C:4]([OH:45])=[O:3])=[O:9])=[O:21])[C:23]4[CH:24]=[CH:25][CH:26]=[N:27][C:28]=4[C:29]=3[OH:44])[CH2:32]2)=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 73046845HCID 73046845, compound

Product 1

HCID 85123690HCID 85123690, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-[(2-{[7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carbonyl]-amino}-ethyl)-phenoxy-phosphinoyloxy]-propionic acid ethyl ester 221 (15 mg, 0.024 mmol) dissolved in acetonitrile (0.10 ml) and water (0.05 ml) was added 1.0 M NaOH (0.072 ml). The reaction mixture was stirred at room temperature for 3 hours, cooled to 0° C., and quenched with 1.0 M HCl (0.1 ml). The mixture was concentrated in vacuo and the resulting residue was redissolved in dimethylsulfoxide, filtered through a glass plug, and purified by reverse phase preparatory HPLC to afford 2-[(2-{[7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carbonyl]-amino}-ethyl)-hydroxy-phosphinoyloxy]-propionic acid 315 (9 mg, 0.014 mmol, 60%). 1H NMR (CD3OD) δ 9.0 (d, 1H), 8.80 (d, 1H), 7.80 (m, 1H), 7.42 (M, 2H), 7.10 (t, 2H), 4.80 (d, 2H), 4.62 (s, 2H), 3.75 (m, 2H), 2.20 (m, 2H), 1.46 (d, 3H). 3P δ 27.8. 19F δ −78.0, −118.0. MS: 532.1 (M+1).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with 1.0 M HCl (0.1 ml)
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe resulting residue was redissolved in dimethylsulfoxide
  5. filtrationfiltered through a glass plug
  6. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-1a4967c619e246f6a5b81f252d205b4a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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