Hydrochloric Acid → 3-{[(Diphenylmethyl)carbamoyl]amino}propane-1-sulfonic acid
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][S:5]([OH:8])(=[O:7])=[O:6].[OH-].[Na+].[C:11]1([CH:17]([N:24]=[C:25]=[O:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>>[CH:17]([NH:24][C:25]([NH:1][CH2:2][CH2:3][CH2:4][S:5]([OH:8])(=[O:7])=[O:6])=[O:26])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
The 3-amino-1-propanesulfonic acid (1.0 g, 7.2 mmol) was dissolved in 3N NaOH (370 mg, 9.4 mmol in 3 mL of water). After the solution was cooled to 0° C., diphenylmethyl isocyanate (1.4 mL, 7.2 mmol) was added. The reaction mixture was allowed to warm up to room temperature, stirred for 8 h (r.t.), and followed by addition of 3N NaOH (3 mL). The reaction mixture was stirred for 18 h. The pH of the reaction mixture was brought to 3 with 5N HCl. The solvent was evaporated under reduced pressure. EtOH (15 mL) was added and the mixture was stirred at reflux for 30 sec. The hot mixture was filtered. The filtrate was evaporated to dryness. This process was repeated 2 more times. The final product was dried in vacuo, affording compound AF, 837 mg (34%).
Workup
- temperatureto warm up to room temperature
- stirringThe reaction mixture was stirred for 18 h
- customThe solvent was evaporated under reduced pressure
- additionEtOH (15 mL) was added
- stirringthe mixture was stirred
- temperatureat reflux for 30 sec
- filtrationThe hot mixture was filtered
- customThe filtrate was evaporated to dryness
- dry with materialThe final product was dried in vacuo
- customaffording compound AF, 837 mg (34%)
Sources & evidence
- ORD record
- ord-07e8e7e15ab640379afffc2860e27bff
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642801B2
Reaction notes
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