Water → HCID 90396916, compound

HRID 717321Notes

Reaction equation

HRID 717321 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C@:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([OH:9])[C:6]([OH:8])=O)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:43][C:44]1[CH:45]=[C:46]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:47]=[CH:48][C:49]=1[NH2:50].O>CN(C=O)C.C(OCC)(=O)C>[NH2:43][C:44]1[CH:45]=[C:46]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:47]=[CH:48][C:49]=1[NH:50][C:6](=[O:8])[C@@:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([OH:9])[C:4]([O:3][CH2:1][CH3:2])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12709656N-(3,4-diaminophenyl)methanesulfonamideHCID 89500113HCID 89500113, compound

Product 1

HCID 90396916HCID 90396916, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-3-ethoxy-2-(4-fluorobenzyl)-2-hydroxy-3-oxopropanoic acid (1.28 g, 5 mmol), HATU (1.9 g 5 mmol), N-(3,4-diaminophenyl) methanesulfonamide (1 g, 5 mmol) in 4 mL of DMF was stirred at rt overnight. To this mixture was added water (20 ml) and ethyl acetate (50 ml). The organic layer was separated and washed with water (10 ml) and then concentrated in vacuo after being dried over anhydrous MgSO4. The residue was purified by PREP-HPLC to give the product as white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (10 ml)
  3. concentrationconcentrated in vacuo
  4. dry with materialafter being dried over anhydrous MgSO4
  5. customThe residue was purified by PREP-HPLC

Sources & evidence

ORD record
ord-3dbd129901e849be9020633b7bf59234
Source dataset
uspto-grants-2015_11
Patent number
US09193717B2

Reaction notes

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