Acetic Acid → HCID 178426929, compound

HRID 1725165Notes

Reaction equation

HRID 1725165 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:7]=[C:6]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([C:25]2[CH:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[O:24])[CH:17]=1.CS(C)=O.C(O)(=O)C.O.[NH2:41][C:42]([NH2:44])=[NH:43]>>[NH:43]([C:3](=[O:2])[CH2:4][N:5]1[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=[C:6]1[C:16]1[CH:17]=[C:18]([NH:22][C:23]([C:25]2[CH:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[O:24])[CH:19]=[CH:20][CH:21]=1)[C:42]([NH2:44])=[NH:41]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 3520GuanidineHCID 57423682HCID 57423682, compound

Product 1

HCID 178426929HCID 178426929, compound

Procedure

The residue from step 3 is dissolved in 300 μl guanidine in dimethylsulfoxide (500 μmoles) and agitated in a shaker at room temperature for 1-4 h. The reaction is quenched with excess acetic acid (ca. 1 mmole), DMSO (200 uL) and water (100 uL), and concentrated in vacuo. The residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total) and purified by Gilson preparative HPLC system, Retention Time, 0.76 min., M+H 443.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total)
  3. custompurified by Gilson preparative HPLC system, Retention Time, 0.76 min., M+H 443

Sources & evidence

ORD record
ord-c243f58a91664abd8d8fa18b11196eda
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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