Hydrochloric Acid → HCID 86759750, compound

HRID 2184220Notes

Reaction equation

HRID 2184220 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:7][S:8]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:4]([OH:6])=[O:5].[ClH:21].[CH2:22](O)[CH3:23]>>[ClH:21].[NH2:1][CH2:2][C@H:3]([NH:7][S:8]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:4]([O:6][CH2:22][CH3:23])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 60004411HCID 60004411, compound

Product 1

HCID 86759750HCID 86759750, compound

Conditions

Temperature
35 °C

Procedure

147.2 g (0.5 mol) of (2S)-3-amino-2-(naphthalene-1-sulfonylamino)propionic acid were suspended in 1 l of ethanol and hydrogen chloride gas was introduced into the mixture for about 2 h whereupon the temperature increased to about 35° C. and a clear solution was obtained. Then the mixture was evaporated in vacuo in a rotary evaporator. The residue was dissolved in hot ethanol and diisopropyl ether was added until precipitation of the product started. The product was allowed to crystallize overnight at room temperature. The title hydrochloride was filtered off, washed with diisopropyl ether and dried in vacuo. Yield: 148 g (83%).

Workup

  1. customa clear solution was obtained
  2. customThen the mixture was evaporated in vacuo in a rotary evaporator
  3. dissolutionThe residue was dissolved in hot ethanol
  4. additiondiisopropyl ether was added until precipitation of the product
  5. customto crystallize overnight at room temperature
  6. filtrationThe title hydrochloride was filtered off
  7. washwashed with diisopropyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-52e9f4806af4456891c280b210797b0c
Source dataset
uspto-grants-2005_05
Patent number
US06900318B1

Reaction notes

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