Diethyl Ether → HCID 13652720, compound

HRID 980603Notes

Reaction equation

HRID 980603 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([NH:29][C@@H:30]2[C:36](=[O:37])[N:35]([CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])[C:34]3[CH:46]=[CH:47][CH:48]=[CH:49][C:33]=3[S:32][CH2:31]2)[C:24]([O:26]CC)=[O:25])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)(=O)C.Br.C(OCC)C>C(O)(=O)C>[C:24]([C@@H:23]([NH:29][C@@H:30]1[C:36](=[O:37])[N:35]([CH2:38][C:39]([OH:41])=[O:40])[C:34]2[CH:46]=[CH:47][CH:48]=[CH:49][C:33]=2[S:32][CH2:31]1)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 53690439HCID 53690439, compound

Product 1

HCID 13652720HCID 13652720, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 1.5 ml of acetic acid is dissolved 0.3 g of tertbutyl 3(R)-[7-(1-benzyloxycarbonyl-4-piperidyl)-1(S)-ethoxycarbonylheptyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, and 1 ml of 30% hydrogen-bromide acetic acid solution is added to the solution, followed by allowing the mixture to stand at room temperature for 0.5 hour. Ethyl ether (80 ml) is added to the reaction solution, which is then allowed to stand. The supernatant liquid is decanted, and the precipitate is dissolved in 10 ml of 1N aqueous sodium hydroxide solution, followed by allowing the solution to stand at room temperature for 30 minutes. The solution is neutralized with 2 ml of acetic acid, and purified by XAD-2 column chromatography (water:methanol=1:1). The eluent is concentrated under reduced pressure, and the residue is lyophilized to give 0.1 g of 3(R)-[1(S)-carboxy-7-(4-piperidyl)heptyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid as a colorless powder.

Workup

  1. additionis added to the solution
  2. customThe supernatant liquid is decanted
  3. dissolutionthe precipitate is dissolved in 10 ml of 1N aqueous sodium hydroxide solution
  4. waitto stand at room temperature for 30 minutes
  5. custompurified by XAD-2 column chromatography (water:methanol=1:1)
  6. concentrationThe eluent is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d4689beb45dc4516bcf93d2eb7177acc
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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