Ethyl Acetate → HCID 66847153, compound

HRID 58367Notes

Reaction equation

HRID 58367 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-8733e473152a41e591953f999b28f39c
Source dataset
uspto-grants-2016_09
Patent number
US09434762B2

Reaction notes

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