Triethylamine → HCID 131723069, compound

HRID 1249929Notes

Reaction equation

HRID 1249929 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](=[C:16]([Cl:21])[CH:17]=[CH:18][CH:19]=2)[CH2:14][C@H:13]1[C:22]([OH:24])=O)=[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)C>[F:28][C:29]([F:33])([F:32])[CH2:30][NH:31][C:22]([CH:13]1[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[N:12]1[C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:25][CH3:26])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 20716542HCID 20716542, compound

Product 1

HCID 131723069HCID 131723069, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-(N-t-Butoxycarbonyl-2(S)-aminobutyryl)-4-chloroindoline-2(S)-carboxylic acid (0.2 g, 0.52 mmol) and 2,2,2-trifluoroethylamine hydrochloride (0.142 g, 1.0 mmol) were dissolved in dried dichloromethane (10 ml) under nitrogen at 0° C., and triethylamine (0.44 ml, 3 mmol) was added followed by bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.265 g, 1.0 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 95:5 dichloromethane: diethyl ether as eluent 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

Sources & evidence

ORD record
ord-20b8338624a845cf98e7874016865a73
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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