Phenoxyacetic Acid → HCID 16736346, compound

HRID 1991400Notes

Reaction equation

HRID 1991400 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([C@H:21]3[CH2:26][CH2:25][CH2:24][CH2:23][NH:22]3)[O:18][N:17]=2)=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C.O(CC(Cl)=O)C1[CH:42]=[CH:41][CH:40]=[CH:39]C=1.[O:47](CC(O)=O)[C:48]1C=CC=C[CH:49]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:20]=[C:19]([C@H:21]3[CH2:26][CH2:25][CH2:24][CH2:23][N:22]3[C:48](=[O:47])[CH2:49][O:5][C:3]3[CH:2]=[CH:42][CH:41]=[CH:40][CH:39]=3)[O:18][N:17]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 19188Phenoxyacetic AcidHCID 69703Phenoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 68687777HCID 68687777, compound2×HCID 86612873HCID 86612873, compound

Product 1

HCID 16736346HCID 16736346, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Crude material from step 3 was dissolved in 1 ml DMF and 0.1 mmol DIPEA. Either 0.1 mmol phenoxyacetyl chloride were added and the reaction stirred at room temperature for 30 min, or the corresponding phenoxyacetic acid derivatives were pre-activated with HATU/DIPEA in DMF for lOmin and added to the crude material from step 3. The product was isolated via preparative high performance liquid chromatography (HPLC).

Workup

  1. customThe product was isolated via preparative high performance liquid chromatography (HPLC)

Sources & evidence

ORD record
ord-3bdcd5983a9b43d5b02987ea1db8faaa
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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