Water → (2S)-N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanamide

HRID 216290Notes

Reaction equation

HRID 216290 reaction equation
[N:1]([CH2:4][C@@H:5]([OH:34])[C@@H:6]([NH:14][C:15](=[O:33])[C@@H:16]([N:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[N:27]=[C:28]([CH3:31])[S:29][CH:30]=2)[C:21]1=[O:32])[CH:17]([CH3:19])[CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH2:4][C@@H:5]([OH:34])[C@@H:6]([NH:14][C:15](=[O:33])[C@@H:16]([N:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[N:27]=[C:28]([CH3:31])[S:29][CH:30]=2)[C:21]1=[O:32])[CH:17]([CH3:19])[CH3:18])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86598721(2S)-N-[(1S,2R)-3-azido-1-benzyl-2-hydroxypropyl]-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanamide

Product 1

HCID 66891621(2S)-N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanamideYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of the product of Example 274B (1.3 g) in tetrahydrofuran:water (25 mL, 4:1) was treated with triphenylphosphine (1.4 g, 2 equivalents), stirred at 70° C. for 2 hours and concentrated. The residue was partitioned between 1N HCl and dichloromethane. The aqueous layer was separated and made basic using 1N NaOH, extracted with dichloromethane and the organic extract was concentrated. The residue was purified by HPLC reverse phase chromatography using water (0.1% trifluoroacetic acid):acetonitrile (95:5) to acetonitrile (100%) to give 0.76 g (62%) of the title compound.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 1N HCl and dichloromethane
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane
  5. extractionthe organic extract
  6. concentrationwas concentrated
  7. customThe residue was purified by HPLC reverse phase chromatography

Sources & evidence

ORD record
ord-c6fffb7eff444a999dca5a7f74415b78
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

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