Sodium Hydroxide → HCID 58935428, compound

HRID 32351Notes

Reaction equation

HRID 32351 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-396bb6efca284c448013a19c921a230d
Source dataset
uspto-grants-2008_09
Patent number
US07427611B2

Reaction notes

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