Hydrochloric Acid → HCID 54570593, compound

HRID 1005587Notes

Reaction equation

HRID 1005587 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH:11]1[C:23]2[CH:22]([CH2:24][O:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31]Br)=[O:27])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1.Cl>C(O)C.[OH-].[Na+].O>[CH:20]1[C:21]2[CH:22]([CH2:24][O:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1]([OH:10])=[O:9])=[O:27])[C:23]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic AcidHCID 16218514(9H-Fluoren-9-yl)methyl (3-bromopropyl)carbamate

Product 1

HCID 54570593HCID 54570593, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of thiosalicylic acid (500 mg) in ethanol (15 ml) and 2N sodium hydroxide aqueous solution (3.2 ml) was added 3-(9-fluorenylmethoxycarbonylamino)-propyl bromide at ambient temperature and the suspension was stirred for 2 hours. The resulting clear solution was diluted with water (20 ml) and acidified with 1N hydrochloric acid (6.5 ml). White crystals were collected by filtration and the solid was washed with ethanol-water (1:3, 15 ml) and then with n-hexane - diethyl and either (2:1, 15 ml) to give 2-[3-(9-fluorenylmethoxycarbonylamino)-propylthio]benzoic acid (1.07 g).

Workup

  1. filtrationWhite crystals were collected by filtration
  2. washthe solid was washed with ethanol-water (1:3, 15 ml)

Sources & evidence

ORD record
ord-f9282cbd832146b99b43d708bec6b58c
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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