Triethylamine → HCID 131723073, compound

HRID 1249935Notes

Reaction equation

HRID 1249935 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:26][CH3:27])[C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14][C@H:13]1[C:23]([OH:25])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[F:29][C:30]([F:34])([F:33])[CH2:31][NH2:32].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl.C(OCC)(=O)C>[F:29][C:30]([F:34])([F:33])[CH2:31][NH:32][C:23]([CH:13]1[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[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])[CH2:26][CH3:27])=[O:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 20716553HCID 20716553, compound

Product 1

HCID 131723073HCID 131723073, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(N-t-Butoxycarbonyl-2(S)-aminobutyryl)-5-methoxy-indoline-2(S)-carboxylic acid (0.38 g, 1 mmol) and 2,2,2-trifluoroethylamine hydrochloride (0.271 g, 2.0 mmol) were dissolved in dried dichloromethane (20 ml) under nitrogen at 0° C., and triethylamine (0.7 ml, 5 mmol) was added followed by bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.509 g, 2 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 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-e1efb8e6025044a69e0d501001619652
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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