Cyclohexanone → HCID 13454619, compound

HRID 1284951Notes

Reaction equation

HRID 1284951 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:14][C@@H:15]1[C:21](=[O:22])[N:20]([CH2:23][C:24]([OH:26])=[O:25])[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[S:17][CH2:16]1)[C:9]([O:11]CC)=[O:10].[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C([BH3-])#N.[Na+]>C(O)C>[C:9]([C@@H:8]([NH:14][C@@H:15]1[C:21](=[O:22])[N:20]([CH2:23][C:24]([OH:26])=[O:25])[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[S:17][CH2:16]1)[CH2:7][CH2:6][CH2:5][CH2:4][NH:3][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 13454603HCID 13454603, compound

Product 1

HCID 13454619HCID 13454619, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3(R)-[5-amino-1(S)-ethoxycarbonylpentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid dihydrochloride (0.2 g) obtained in Example 59, ethanol (10 ml), cyclohexanone (2 g) and sodium cyanoborohydride (0.3 g) is allowed to stand overnight at room temperature. To the residue, after evaporation of ethanol, is added 1N aqueous sodium hydroxide (4 ml). The resulting mixture is stirred at room temperature for 1 hour, diluted with water (20 ml) and extracted 3 times with ethyl acetate (20 ml each). The aqueous layer is slightly acidified with acetic acid (1 ml) and subjected to Amberlite XAD-2 column chromatography eluting with methanol-water (1:1). The eluate is concentrated under reduced pressure and lyophilized to give 3(R)-[1(S)-carboxy-5-cyclohexylaminopentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid (0.12 g) as colorless powder.

Workup

  1. customTo the residue, after evaporation of ethanol
  2. additionis added 1N aqueous sodium hydroxide (4 ml)
  3. additiondiluted with water (20 ml)
  4. extractionextracted 3 times with ethyl acetate (20 ml each)
  5. washeluting with methanol-water (1:1)
  6. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b308772c93740bfbeced3ababdf850f
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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