Pivalic acid → HCID 58157754, compound

HRID 468681Notes

Reaction equation

HRID 468681 reaction equation
[S:1]1[C:5]2[CH2:6][NH:7][CH2:8][C:4]=2[CH:3]=[C:2]1[C:9]([O:11][CH3:12])=[O:10].[C:13](O)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN1CCOCC1>C(Cl)Cl>[C:13]([N:7]1[CH2:8][C:4]2[CH:3]=[C:2]([C:9]([O:11][CH3:12])=[O:10])[S:1][C:5]=2[CH2:6]1)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6417Pivalic acidHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 55252787HCID 55252787, compound

Product 1

HCID 58157754HCID 58157754, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of methyl 5,6-dihydro-4H-thieno[2,3-c]pyrrole-2-carboxylate (0.023 g, 0.127 mmol) and pivalic acid (0.014 g, 0.14 mmol) in methylene chloride (0.92 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.055 g, 0.146 mmol) and N-methylmorpholine (0.035 mL, 0.32 mmol) respectively. The reaction mixture was stirred at room temperature overnight. The reaction was diluted with additional DCM (2 mL) and washed with saturated aqueous NaHCO3 (2 mL). The aqueous layer was extracted with additional DCM (3 mL), and the combined organic layers were concentrated to afford an oily residue. LCMS (FA) ES+ 268.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2 mL)
  2. extractionThe aqueous layer was extracted with additional DCM (3 mL)
  3. concentrationthe combined organic layers were concentrated
  4. customto afford an oily residue

Sources & evidence

ORD record
ord-7be06914e0df4c5eac27db6837dae578
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Reaction notes

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