Triethylamine → HCID 131723066, compound

HRID 1249924Notes

Reaction equation

HRID 1249924 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:39][CH3:40])[C:17]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:26]=2)[CH2:21][C@H:20]1[C:36](O)=[O:37])=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].Cl.[F:42][C:43]([F:47])([F:46])[CH2:44][NH2:45].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[F:42][C:43]([F:47])([F:46])[CH2:44][NH:45][C:36]([CH:20]1[CH2:21][C:22]2[C:27](=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:23]=2)[N:19]1[C:17](=[O:18])[C@@H:16]([NH:15][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:39][CH3:40])=[O:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 20716549HCID 20716549, compound

Product 1

HCID 131723066HCID 131723066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (4.9 mL, 33 mmol) was added to the solution of 1-(N-t-butoxycarbonyl-2(S)-aminobutyryl)-5-benzyloxyindoline-2(S)-carboxylic acid (2.6 g, 5.72 mmol) and 2,2,2-trifluoroethylamine hydrochloride (1.55 g, 11.4 mmol) in dried dichloromethane (50 mL) at 0° C. under nitrogen, followed by bis(2-oxo-3-oxazolidinyl)phosphinic chloride (2.902 g, 11.4 mmol). The temperature was allowed to rise to room temperature and the mixture was stirred at room temperature for twenty-four hours, then filtered. The filtrate was concentrated under vacuum to give a brown solid which was purified by column chromatography (silica gel, 8:2 diethyl ether: petroleum spirit) to provide a white solid as the desired product.

Workup

  1. customto rise to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. customto give a brown solid which
  5. customwas purified by column chromatography (silica gel, 8:2 diethyl ether: petroleum spirit)

Sources & evidence

ORD record
ord-8190d8e3a51b4bfcbd764a8ac5c04cd8
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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