Hydrochloric Acid → HCID 19081081, compound

HRID 234850Notes

Reaction equation

HRID 234850 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([C:24](O)=[O:25])[NH:10][S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.O.[ClH:35].[N:36]1C=CC=CC=1>>[ClH:35].[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[S:11]([NH:10][CH:9]([CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:24]([NH2:36])=[O:25])(=[O:12])=[O:13]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10384536HCID 10384536, compound

Product 1

HCID 19081081HCID 19081081, compound

Procedure

A solution. of.0.7 g of 3-(p-aminophenyl)-N-(2-naphthylsulfonyl)-D-alanine (Example 35a) in 5 ml of pyridine is treated with 1 ml of acetic anhydride and left to stand at room temperature for 20 hours. After the addition of water and conc. HCl (ice-cooling) the separated product is filtered off under suction, dissolved in ethyl acetate, washed with water, dried and evaporated. The product is dissolved in 20 ml of methanolic 1N NaOH and left to stand. The solution is evaporated, the residue is dissolved in water, acidified with conc. HCl, the precipitated product is filtered off under suction, dissolved in ethyl acetate and washed with water. After evaporation the residue is reacted analogously to Example 5 and gives 146 mg of (R)-p-acetamido-N-[(RS)-1-amidino-3-piperidinyl]methyl]-α-(2-naphthylsulfonamido)hydrocinnamamide hydrochloride, FAB-MS: 551 (M+H)+.

Workup

  1. waitleft
  2. filtrationis filtered off under suction
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. dissolutionThe product is dissolved in 20 ml of methanolic 1N NaOH
  8. waitleft
  9. customThe solution is evaporated
  10. dissolutionthe residue is dissolved in water
  11. filtrationthe precipitated product is filtered off under suction
  12. dissolutiondissolved in ethyl acetate
  13. washwashed with water
  14. customAfter evaporation the residue
  15. customis reacted analogously to Example 5

Sources & evidence

ORD record
ord-4b01d07edf35406f93af3d607c34ad15
Source dataset
uspto-grants-1997_01
Patent number
US05595999

Reaction notes

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