Hydrochloric Acid → HCID 22840185, compound

HRID 868248Notes

Reaction equation

HRID 868248 reaction equation
Cl.Cl.C([O:5][C:6]([C@@H:8]([NH:19][C@H:20]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][N:22]([CH2:33][C:34]([OH:36])=[O:35])[C:21]1=[O:37])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:7])C.[OH-].[Na+].Cl>>[C:6]([C@@H:8]([NH:19][C@H:20]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:23][N:22]([CH2:33][C:34]([OH:36])=[O:35])[C:21]1=[O:37])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([OH:7])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67825398HCID 67825398, compound

Product 1

HCID 22840185HCID 22840185, compoundYield 90.7%

Procedure

A solution of 300 mg of rel-α-{3(S)-[1(S)ethoxycarbonyl-5-(4-piperidyl)pentylamino]-2-oxo-6(R)-phenylperhydroazepin-1-yl}acetic acid dihydrochloride (prepared as described in Example 22) in 3.2 ml of a 1N aqueous solution of sodium hydroxide was stirred for 16 hours at room temperature, and then its pH value was adjusted to a value of 4.5 by adding 1N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dissolved again in water containing a small amount of acetic acid. The resulting solution together with the filtrate was poured onto a column pached with a porous resin HP-20 (Mitsubishi Kasei Kogyo Co., Ltd.) and eluted first with water and then with 20% v/v aqueous acetone. The fractions first eluted with water contained sodium chloride and acetic acid, whilst the fractions eluted next with 20% v/v aqueous acetone contained the title compound. The latter fractions were concentrated by evaporation under reduced pressure to give 223 mg of the title compound as a powdery substance.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutiondissolved again in water containing a small amount of acetic acid
  3. additionThe resulting solution together with the filtrate was poured onto a column
  4. wash(Mitsubishi Kasei Kogyo Co., Ltd.) and eluted first with water
  5. washThe fractions first eluted with water
  6. washwhilst the fractions eluted next with 20% v/v aqueous acetone
  7. concentrationThe latter fractions were concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-baa9f218289f42d5b2c8a7ae4ae9dfad
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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