Triethylamine → HCID 131723261, compound

HRID 2185673Notes

Reaction equation

HRID 2185673 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)[CH2:12][CH2:11]O1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]([C:34]([OH:36])=O)[CH2:28]2.[CH2:37]([O:44][C:45]([NH:47][C@H:48]([C:52]([OH:54])=O)[CH:49]([CH3:51])[CH3:50])=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>ClCCl>[CH2:6]([NH:3][C:34]([CH:29]1[CH2:28][C:27]2[C:31](=[CH:32][CH:33]=[C:25]([O:24][CH3:23])[CH:26]=2)[N:30]1[C:52](=[O:54])[C@H:48]([CH:49]([CH3:50])[CH3:51])[NH:47][C:45]([O:44][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:46])=[O:36])[CH2:7][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 726987N-Carbobenzoxy-L-valineHCID 128420435-Methoxy-2,3-dihydro-1H-indole-2-carboxylic acid

Product 1

HCID 131723261HCID 131723261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.25 ml, 16 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinyl chloride (1.539 g, 6.054 mmol) were added to a cooled solution (0° C.) of 5-methoxyindoline-2(R/S)-carboxylic acid (1.000 g, 4.03 mmol) and N-benzyloxycarbonyl-L-valine (1.135 g, 4.50 mmol) dissolved in dichloromethane (50 ml), under nitrogen. The mixture was stirred at room temperature for 22 hours and then washed with 10% citric acid (3×50 ml), 5% NaHCO3 (3×50 ml) and water (50 ml). The organic. phase was dried and concentrated: the residue was purified by chromatography on a column of silica gel, using a 3/2 petroleum ether/ethyl acetate mixture as eluent. A white solid was obtained.

Workup

  1. washwashed with 10% citric acid (3×50 ml), 5% NaHCO3 (3×50 ml) and water (50 ml)
  2. customphase was dried
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on a column of silica gel
  5. customA white solid was obtained

Sources & evidence

ORD record
ord-9b745731ff794ff98518c7e8113b19d3
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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