Phenylacetic Acid → HCID 178453619, compound

HRID 1524877Notes

Reaction equation

HRID 1524877 reaction equation
C(OC(=O)N[C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:41])[NH:15][C@H:16]([C:27]2[NH:28][CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([F:40])[CH:33]=3)[N:31]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)[CH2:10][CH2:9]1)(C)(C)C.[C:43]1([CH2:49][C:50]([OH:52])=O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.N1[CH:58]=[CH:57][CH:56]=CC=1.C1C=C[C:62]2[N:67](O)N=NC=2C=1.[CH3:69]CN=C=NCCCN(C)C.CC[O:82][C:83](C)=[O:84]>CN(C=O)C>[C:57]([O:84][C:83](=[O:82])[NH:67][CH2:62][C@H:8]1[CH2:9][CH2:10][C@H:11]([C:14](=[O:41])[NH:15][C@H:16]([C:27]2[NH:28][CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([F:40])[CH:33]=3)[N:31]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:24][C:50](=[O:52])[CH2:49][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:12][CH2:13]1)([CH3:56])([CH3:58])[CH3:69]

Participants

8

Reactant 6

HCID 999Phenylacetic AcidHCID 1049PyridineHCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178453970HCID 178453970, compound

Product 1

HCID 178453619HCID 178453619, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 159 Part B (132 mg, 0.23 mmol) and phenyl acetic acid (40 mg, 0.28 mmol) were dissolved in pyridine (0.7 mL, 0.71 mmol) and 1.5 mL of DMF. HOBt (45 mg, 0.3 mmol) and EDCI (60 mg, 0.30 mmol) were added to the flask, and the reaction was stirred at rt for 12 h. The reaction was diluted with EtOAc, extracted with ½ sat. brine (4-6 times), dried over MgSO4, filtered and evaporated to dryness to yield the desired product 150 mg (95% yield). MS 677 (M−H)−.

Workup

  1. extractionextracted with ½ sat. brine (4-6 times)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-cb8a3842600949d6aec478e54537dca5
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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