Sodium Hydroxide → 2-{[1-({[(3S)-1-(2-tert. butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric Acid

HRID 2218073Notes

Reaction equation

HRID 2218073 reaction equation
[C:1]([O:5][C:6](=[O:42])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C@H:10]([NH:19][C:20]([C:22]2([CH2:27][CH:28]([CH2:34][C:35]([NH:37][CH:38]([CH3:40])[CH3:39])=[O:36])[C:29]([O:31]CC)=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[C:9]1=[O:41])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].OS([O-])(=O)=O.[K+]>C(O)C.O>[C:1]([O:5][C:6](=[O:42])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C@H:10]([NH:19][C:20]([C:22]2([CH2:27][CH:28]([CH2:34][C:35]([NH:37][CH:38]([CH3:39])[CH3:40])=[O:36])[C:29]([OH:31])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[C:9]1=[O:41])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 58935425Ethyl 2-{[(3S)-1-({[1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyrate

Product 1

HCID 589354242-{[1-({[(3S)-1-(2-tert. butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric AcidYield 88.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.6 g ethyl 2-{[(3S)-1-({[1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyrate (for preparation see Example 1) was dissolved in 52 ml of ethanol. A solution of 710 mg solid NaOH in 52 ml water was added to this receiving solution. After 30 minutes, it was acidulated with dilute aqueous KHSO4 solution to approximately pH 2 and the aqueous phase was extracted three times with 50 ml EA each time. The combined organic phases were dried over magnesium sulfate, the solvent was largely evaporated at reduced pressure and the remaining residue was chromatographed on silica gel (mobile phase: EA/cyclohexane 2:1 v/v). Drying the product fractions in an oil pump vacuum (5×10−2 mbar) yielded 2.2 g of the title compound as white foam resin, MS: [M+H]+: 558; m/z: 502, 425, 397, 323.

Workup

  1. extractionthe aqueous phase was extracted three times with 50 ml EA each time
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customthe solvent was largely evaporated at reduced pressure
  4. customthe remaining residue was chromatographed on silica gel (mobile phase: EA/cyclohexane 2:1 v/v)
  5. customDrying the product fractions in an oil pump vacuum (5×10−2 mbar)

Sources & evidence

ORD record
ord-408bb781c6b9416c8886dfb2d987e1a9
Source dataset
uspto-grants-2008_08
Patent number
US07410962B2

Reaction notes

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