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Ethyl Acetate → (S)-2-{(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-(4-fluoro-benzenesulfonylamino)-propionylamino]-4-methyl-pentanoylamino}-pent-4-enoic acid methyl ester

HRID 2371308
Notes
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Reaction equation

HRID 2371308 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:13]([NH:15][C@@H:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]([OH:19])=O)=[O:14])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].CN(C(ON1N=N[C:45]2[CH:46]=CC=N[C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:61](C(C)C)C(C)C.C[CH2:69][O:70][C:71]([CH3:73])=[O:72]>CN(C=O)C>[CH3:69][O:70][C:71](=[O:72])[C@@H:73]([NH:61][C:17](=[O:19])[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:24][S:25]([C:28]1[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][CH:7]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:46][CH:45]=[CH2:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 66846978HCID 66846978, compound

Product 1

HCID 66846969
(S)-2-{(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-(4-fluoro-benzenesulfonylamino)-propionylamino]-4-methyl-pentanoylamino}-pent-4-enoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carboxylic acid 12 (2.50 g, 5.08 mmol), HATU (2.13 g, 5.59 mmol) and (S)-allyl-glycine methyl ester hydrochloride (0.925 g, 5.59 mmol) were dissolved in DMF (30 mL). DIPEA was added (3.54 mL, 20.3 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. Purification was achieved using flash chromatography, eluting with a gradient of (50/70) petroleum ether to 2/1 EtOAc/(50/70) petroleum ether to yield a white solid, 2.70 g, 89%. Rf=0.38 (1/1 EtOAc/(50/70) petroleum ether).

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. customPurification
  7. washeluting with a gradient of (50/70) petroleum ether to 2/1 EtOAc/(50/70) petroleum ether
  8. customto yield a white solid, 2.70 g, 89%

Sources & evidence

ORD record
ord-04bf3d20d7d1431ba9b726785779c9c8
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08710178B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes