Triethylamine → HCID 53676026, compound

HRID 1249919Notes

Reaction equation

HRID 1249919 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:25][CH3:26])[C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[CH2:14][C@H:13]1[C:22](O)=[O:23])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[F:28][C:29]([F:33])([F:32])[CH2:30][NH2:31].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl.C(OCC)(=O)C>[F:28][C:29]([F:33])([F:32])[CH2:30][NH:31][C:22]([C@@H:13]1[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[N:12]1[C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:25][CH3:26])=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 10915949HCID 10915949, compound

Product 1

HCID 53676026HCID 53676026, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(N-t-Butoxycarbonyl-2(S)-aminobutyryl)-5-chloroindoline-2(S)-carboxylic acid (0.192 g, 0.5 mmol) and 2,2,2-trifluoroethylamine hydrochloride (0.205 g, 1.5 mmol) were dissolved in dried dichloromethane (5 ml) under nitrogen at 0° C., and triethylamine (0.63 ml, 4.5 mmol) was added followed by bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.382 g, 1.5 mmol). 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 vacuum to give a brown solid which was columned on silica gel using 7:3 petroleum spirit: ethyl acetate as eluent to provide a white solid.

Workup

  1. customto rise to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. customto give a brown solid which

Sources & evidence

ORD record
ord-400c4bfbf1934e33b302c195a0fc5ecb
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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