Ethyl Acetate → HCID 66847153, compound

HRID 2371313Notes

Reaction equation

HRID 2371313 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:14]([NH:16][C@@H:17]([CH2:21][CH:22]([CH3:24])[CH3:23])C(O)=O)=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].C[N:34]([C:36]([O:40]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)[CH:60]([CH3:62])[CH3:61].C[CH2:67][O:68][C:69]([CH3:71])=[O:70]>CN(C=O)C>[CH3:67][O:68][C:69](=[O:70])[C@@H:71]([NH:34][C:36](=[O:40])[C@@H:17]([NH:16][C:14](=[O:15])[C@@H:13]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH:3]=[CH2:4])=[CH:11][CH:10]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:62][CH:60]=[CH2:61]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66847077(S)-2-[(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid

Product 1

HCID 66847153HCID 66847153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carboxylic acid 21 (2.14 g, 4.77 mmol), HATU (2.00 g, 5.25 mmol) and (S)-allyl-glycine methyl ester hydrochloride (0.870 g, 5.25 mmol) were dissolved in DMF (30 mL). DIPEA was added (3.32 mL, 19.1 mmol) and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The organic phase was washed sequentially with 1M hydrochloric acid and brine before being dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 2.24 g, 84%. Rf=0.32 (1/1 EtOAc/(50/70) petroleum ether). m.p. 166-168° C.

Workup

  1. custombefore being partitioned between EtOAc and 1M hydrochloric acid
  2. washThe organic phase was washed sequentially with 1M hydrochloric acid and brine
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
  7. customto yield a white solid, 2.24 g, 84%

Sources & evidence

ORD record
ord-4efb7ed7ae66413e98ac7b8cbd2c52ce
Source dataset
uspto-grants-2014_04
Patent number
US08710178B2

Reaction notes

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