Pyridine → 4-[4-(5-tert-Butyl-thiazol-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 605189Notes

Reaction equation

HRID 605189 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:26]=[CH:25][C:12]([C:13]([NH:15][C:16]3[S:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][N:20]=3)=[O:14])=[CH:11][C:10]=2[N+:27]([O-:29])=[O:28])=[CH:4][CH:3]=1.[CH:30]1[C:42]2[CH:41]([CH2:43][O:44][C:45](Cl)=[O:46])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1.N1C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C>[CH:30]1[C:42]2[CH:41]([CH2:43][O:44][C:45](=[O:46])[NH:1][C:2]3[CH:3]=[CH:4][C:5]([S:8][C:9]4[CH:26]=[CH:25][C:12]([C:13](=[O:14])[NH:15][C:16]5[S:17][C:18]([C:21]([CH3:24])([CH3:22])[CH3:23])=[CH:19][N:20]=5)=[CH:11][C:10]=4[N+:27]([O-:29])=[O:28])=[CH:6][CH:7]=3)[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 343679-Fluorenylmethyl chloroformateHCID 866155524-(4-Amino-phenylsulfanyl)-N-(5-tert-butyl-thiazol-2-yl)-3-nitro-benzamide

Product 1

HCID 866155534-[4-(5-tert-Butyl-thiazol-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl-carbamic acid 9H-fluoren-9-ylmethyl esterYield 98.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the product of Example 161B (226 mg, 0.5274 mmol) in anhydrous methylene chloride (5 mL) was treated with 9-fluorenylmethoxycarbonyl chloride (164 mg, 0.6329 mmol) and dry pyridine (0.085 mL, 1.055 mmol), and the resulting yellow solution stirred under a nitrogen atmosphere at ambient temperature for 3 hours. The reaction was diluted with ethyl acetate (100 mL) and washed with water (2×50 mL) and brine (50 mL). The organic was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo to provide the title compound as a yellow solid (338 mg, 98%).

Workup

  1. washwashed with water (2×50 mL) and brine (50 mL)
  2. dry with materialThe organic was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation in vacuo

Sources & evidence

ORD record
ord-21396c24e9ab44a694fbaff037662b1f
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…