Trifluoroacetic acid → HCID 118512009, compound

HRID 1056129Notes

Reaction equation

HRID 1056129 reaction equation
[NH2:1][C@@H:2]([C:13]1[N:14]([S:21]([C:24]2[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:15]=[CH:16][C:17]=1[C:18]([OH:20])=O)[CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CCOC(C)=O>[CH2:6]([O:5][CH2:4][CH2:3][C@@H:2]1[C:13]2[N:14]([S:21]([C:24]3[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=3)(=[O:22])=[O:23])[CH:15]=[CH:16][C:17]=2[C:18](=[O:20])[NH:1]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 118511935HCID 118511935, compound

Product 1

HCID 118512009HCID 118512009, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-2-(1-amino-3-(benzyloxy)propyl)-1-tosyl-1H-pyrrole-3-carboxylic acid compound with TFA (1:1) (504d, 5.43 g, 10.01 mmol) and DIEA (5.22 mL, 30.0 mmol) in EtOAc (50 mL) was added 1-propanephosphonic acid cyclic anhydride (50 wt. % in EtOAc, 5.96 mL, 10.01 mmol) dropwise via syringe. All solids dissolved to give a light brown solution. After 1 h, the reaction was partitioned between sat'd NaHCO3 and EtOAc. The organic layer was washed with sat'd NaHCO3 once, sat'd NaCl once, and the organics were dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give (R)-6-(2-(benzyloxy)ethyl)-1-tosyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (724e) (3.51 g, 8.55 mmol, 85% yield) as a light brown foam. m/z (ESI, +ve) 411.1 (M+Na)+.

Workup

  1. dissolutionAll solids dissolved
  2. customto give a light brown solution
  3. customthe reaction was partitioned between sat'd NaHCO3 and EtOAc
  4. washThe organic layer was washed with sat'd NaHCO3 once
  5. dry with materialthe organics were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe4039f99b79436784325189d971d567
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…