Lithium Hydroxide → HCID 86616777, compound

HRID 1725626Notes

Reaction equation

HRID 1725626 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([C:27]([O:29]C)=O)[CH2:12][S:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][NH:16][CH2:17][CH:18]1[CH2:20][CH2:19]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CN1CCOCC1>O1CCCC1.O.CN(C)C=O>[CH:18]1([CH2:17][N:16]2[C:27](=[O:29])[C@H:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:6])([CH3:4])[CH3:5])[CH2:12][S:13][C@@H:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:15]2)[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 79724-MethylmorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 68959411HCID 68959411, compound

Product 1

HCID 86616777HCID 86616777, compoundYield 31.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (63 mg, 1.49 mmol) was added to a solution of methyl N-(tert-butoxycarbonyl)-S-{2-[(cyclopropylmethyl)amino]-1-phenylethyl}-D-cysteinate (507 mg, 1.24 mmol) in tetrahydrofuran (10 mL) and water (2 mL). After 1 h, then mixture was concentrated and azeotroped with toluene (3×) to give the crude acid. Diphenylphosphoryl azide (0.53 ml, 2.48 mmol) was added to a solution of the crude acid and 4-methylmorpholine (0.20 mL, 1.86 mmol) in N,N-dimethylformamide (25 mL). After 4 h, the mixture was concentrated and water was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with water (2×) and saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (5% ethyl acetate/hexanes→20% ethyl acetate/hexanes) gave the title compound (149 mg). MS 377 (M+1).

Workup

  1. concentrationmixture was concentrated
  2. customazeotroped with toluene (3×)
  3. customto give the crude acid
  4. waitAfter 4 h
  5. concentrationthe mixture was concentrated
  6. additionwater was added
  7. extractionThe mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with water (2×) and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by silica gel chromatography (5% ethyl acetate/hexanes→20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-19d9504fbb4b4b9f997d361f57c58241
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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