Sodium Hydroxide → HCID 70079857, compound

HRID 1489798Notes

Reaction equation

HRID 1489798 reaction equation
[C:1]1([NH:7][C:8](=[O:51])[C@H:9]([CH2:47][CH:48]([CH3:50])[CH3:49])[N:10]([CH2:22][P@:23]([O:45]C)([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:44])[C@@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2[C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:24])[C:11](=[O:21])[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([NH:7][C:8](=[O:51])[C@H:9]([CH2:47][CH:48]([CH3:49])[CH3:50])[N:10]([CH2:22][P:23]([OH:45])([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:44])[C@@H:31]2[CH2:35][CH2:34][CH2:33][N:32]2[C:36](=[O:43])[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:24])[C:11](=[O:21])[CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 70080082HCID 70080082, compound

Product 1

HCID 70079857HCID 70079857, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [[(R,S)-methoxy-[N-(N-(benzoyl)-L-prolyl)aminobutyl]phosphinyl]methyl]-4-phenylbutanoyl-L-leucine N-phenylamide (101 mg, 0.14 mmol) in methanol (1 mL) was treated with 2N aqueous sodium hydroxide (0.5 mL) for 3 hours at room temperature. Additional 2N aqueous sodium hydroxide (0.5 mL) was then added, and the mixture was stirred overnight at room temperature. The solvent was removed by evaporation, and the residue was dissolved in water (25 mL). The aqueous solution was extracted with diethyl ether, acidified to ~pH 1 with 6N hydrochloric acid, and extracted with ethyl acetate (3×). The combined organic layers were washed With saturated brine solution, dried (magnesium sulfate), and evaporated. Purification was effected by reverse phase-high performance liquid chromatography using a Waters Prep Nova-Pak HR C18 6 mm column (19×300 mm) (detection at 220 nm; mobile phase: 57% acetonitrile containing 0.1% trifluoroacetic acid-43% water containing 0.1% trifluoroacetic acid; flow rate: 20 mL/min). Evaporation of appropriate fractions gave desired product as an amorphous solid; yield 47 mg; FAB-MS: m/z 703 (M+1),725 (M+Na), 741 (M+K). The 200 MHz NMR spectrum in methanol-d4 was in accord with the desired structure.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in water (25 mL)
  3. extractionThe aqueous solution was extracted with diethyl ether
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic layers were washed With saturated brine solution
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customPurification
  9. customEvaporation of appropriate fractions

Sources & evidence

ORD record
ord-49ebd1157ca04ca4b31741c0ab0cee2b
Source dataset
uspto-grants-1997_10
Patent number
US05679700

Reaction notes

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