Diisopropylethylamine → HCID 89793962, compound

HRID 1056404Notes

Reaction equation

HRID 1056404 reaction equation
[NH2:1][C@@H:2]([C:5]1[N:6]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:7]=[CH:8][C:9]=1[C:10](O)=[O:11])[CH2:3][CH3:4].FC(F)(F)C(O)=O.N[C@@H](C1N(S(C2C=CC(C)=CC=2)(=O)=O)C=CC=1C(O)=O)CC.CCN(C(C)C)C(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CCOC(C)=O>[CH2:3]([C@@H:2]1[C:5]2[N:6]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:7]=[CH:8][C:9]=2[C:10](=[O:11])[NH:1]1)[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 89793960HCID 89793960, compoundHCID 131736425HCID 131736425, compound

Product 1

HCID 89793962HCID 89793962, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-2-(1-aminopropyl)-1-tosyl-1H-pyrrole-3-carboxylic acid compound with TFA (1:1) (505d, 5.64 g, 12.92 mmol) and DIEA (6.74 mL, 38.8 mmol) in EtOAc (50 mL) was added 1-propanephosphonic acid cyclic anhydride (50 wt. % in EtOAc, 7.69 mL, 12.92 mmol) dropwise via syringe. After 20 min, the reaction was judged complete by LCMS. 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-ethyl-1-tosyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (505e, 3.49 g, 11.47 mmol, 89% yield) as an orange-brown foam. m/z (ESI, +ve) 305.1 (M+1)+.

Workup

  1. customThe reaction was partitioned between sat'd NaHCO3 and EtOAc
  2. washThe organic layer was washed with sat'd NaHCO3 once
  3. dry with materialthe organics were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60b9a1c6906f413e8cc8c665b416d0f0
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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