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Triethylamine → HCID 131723263, compound

HRID 2185684
Notes
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Reaction equation

HRID 2185684 reaction equation
[CH2:1]([NH:5][C:6]([CH:8]1[C:16]([CH3:18])([CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:19]([O:26][C:27]([NH:29][C@@H:30]([CH2:34][CH3:35])[C:31](O)=[O:32])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([NH:5][C:6]([CH:8]1[C:16]([CH3:17])([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]1[C:31](=[O:32])[C@@H:30]([NH:29][C:27]([O:26][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:28])[CH2:34][CH3:35])=[O:7])[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acidHCID 77752115HCID 77752115, compound

Product 1

HCID 131723263HCID 131723263, compound

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3,3-Dimethylindoline-2(R/S)-carboxylic acid butylamide (1.000 g, 4.08 mmol) and N-benzyloxycarbonyl-2(S)-aminobutyric acid (1.451 g, 6.12 mmol) were dissolved in dry tetrahydrofuran (25 ml). The solution was cooled to 0° C. and triethylamine (2.44 ml, 13.78 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinyl chloride (2.338 g, 9.183 mmol) were added. The mixture was stirred at room temperature for 22 hours and ethyl acetate (40 ml) was then added, and the mixture was washed with 3N hydrochloric acid (3×50 ml), 5% sodium bicarbonate (3×50 ml) and water (50 ml) and dried over sodium sulphate. After removing the solvent, several successive purifications by chromatography on a column of silica gel gave the product in the form of an off-white solid.

Workup

  1. washthe mixture was washed with 3N hydrochloric acid (3×50 ml), 5% sodium bicarbonate (3×50 ml) and water (50 ml)
  2. dry with materialdried over sodium sulphate
  3. customAfter removing the solvent, several successive purifications by chromatography on a column of silica gel
  4. customgave the product in the form of an off-white solid

Sources & evidence

ORD record
ord-f36c178a9da14e7bb913f65532606823
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06403561B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes