Sodium Hydroxide → HCID 58935428, compound

HRID 855558Notes

Reaction equation

HRID 855558 reaction equation
C([O:5][C:6](=[O:41])[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]([CH2:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][OH:39])=[O:34])[C:29]([O-:31])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[C:9]1=[O:40])(C)(C)C.[OH-].[Na+]>O.C(O)C>[C:6]([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]([CH2:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][OH:39])=[O:34])[C:29]([OH:31])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[C:9]1=[O:40])([OH:41])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86609583HCID 86609583, compound

Product 1

HCID 58935428HCID 58935428, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6.43 g ethyl (2“rel1”)-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-[(3-hydroxypropyl)amino]-4-oxobutyrate (for preparation see Example 5) was dissolved in 140 ml of a 1:1 (v/v) mixture of water and ethanol, and 4.28 g solid NaOH was added thereto with stirring. After 15 h, the solvent was evaporated at reduced pressure, the residue was taken up in 100 ml EA and washed once with 50 ml aqueous KHSO4 solution. The aqueous phase was extracted twice with 30 ml EA each time. The combined organic phases were washed twice with 30 ml aqueous common salt solution each time and dried over sodium sulfate. Evaporation of the solvent yielded 5.41 g of the title compound.

Workup

  1. additionwas added
  2. customthe solvent was evaporated at reduced pressure
  3. washwashed once with 50 ml aqueous KHSO4 solution
  4. extractionThe aqueous phase was extracted twice with 30 ml EA each time
  5. washThe combined organic phases were washed twice with 30 ml aqueous common salt solution each time
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e3e797d05a374b06bf0fbf024815ffd7
Source dataset
uspto-grants-2007_08
Patent number
US07262184B2

Reaction notes

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