Hydrochloric Acid → HCID 19833168, compound

HRID 1639392Notes

Reaction equation

HRID 1639392 reaction equation
Cl.[Cl:2][C:3]1[CH:27]=[CH:26][C:6]2[C:7](=[O:25])[CH2:8][CH2:9][CH2:10][N:11]([C:16]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23])=[O:17])[C:12](=[O:15])[CH2:13][CH2:14][C:5]=2[CH:4]=1.[O:28]1CCCC1>>[C:22]([NH:21][CH2:20][CH2:19][CH2:18][C:16]([NH:11][CH2:10][CH2:9][CH2:8][C:7]([C:6]1[CH:26]=[CH:27][C:3]([Cl:2])=[CH:4][C:5]=1[CH2:14][CH2:13][C:12]([OH:28])=[O:15])=[O:25])=[O:17])(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67929096HCID 67929096, compound

Product 1

HCID 19833168HCID 19833168, compound

Procedure

120 ml of 2N hydrochloric acid are added to a solution of 23.8 g (0.06 ml) of N-[3-[(11-chloro-2,3,5,6,7,8-hexahydro-3,8-dioxo-4-benzazecin-4(1H)-yl)-carbonyl]propyl]acetamide in 240 ml of tetrahydrofuran and the mixture is stirred at room temperature for 8 days. The solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Recrystallization from methanol/ether gives 2-[4-(4-acetamidobutyramido)butyryl]-5-chlorohydrocinnamic acid as beige crystals with melting point 108°.

Workup

  1. concentrationThe solution is concentrated
  2. extractionextracted with methylene chloride/water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customRecrystallization from methanol/ether

Sources & evidence

ORD record
ord-4ff802f8399d42848a63dd80dfa23726
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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