Triethylamine → HCID 53965693, compound

HRID 1249922Notes

Reaction equation

HRID 1249922 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:27][CH3:28])[C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][C@H:16]1[C:24]([OH:26])=O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[F:30][C:31]([F:35])([F:34])[CH2:32][NH2:33].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[F:30][C:31]([F:35])([F:34])[CH2:32][NH:33][C:24]([C@@H:16]1[CH2:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]1[C:13](=[O:14])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 21344928HCID 21344928, compound

Product 1

HCID 53965693HCID 53965693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(N-Benzyloxycarbonyl-2(S)-aminobutyryl)-indoline-2(S)-carboxylic acid (0.382 g, 1 mmol) and 2,2,2-trifluoroethylamine hydrochloride (0.207 g, 1.5 mmol) were dissolved in dried dichloromethane (10 ml), and triethylamine (5.5 mmol) was added, followed by bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.508 g, 2.0 mmol) under nitrogen at 0° C. The temperature was allowed to rise to room temperature and the mixture was stirred at room temperature for 24 hours, then filtered. The filtrate was concentrated under reduced pressure to give a brown solid which was purified by column chromatography on silica gel using 7:3 petroleum spirit: ethyl acetate as eluent to afford a white solid.

Workup

  1. customto rise to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a brown solid which
  5. customwas purified by column chromatography on silica gel using 7:3 petroleum spirit
  6. customethyl acetate as eluent to afford a white solid

Sources & evidence

ORD record
ord-5a55f2d0ae8a438185b834f95e0f30bb
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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