Dimethylformamide → HCID 68281671, compound

HRID 2278524Notes

Reaction equation

HRID 2278524 reaction equation
Cl.CN(C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[C:22]([O:24][CH2:25][CH3:26])=[O:23].CN([CH:30]=[O:31])C>N1C=CC=CC=1>[CH2:25]([O:24][C:22]([CH:14]1[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]1[C:30](=[O:31])[C@H:22]([O:24][CH2:25][C:4]1[CH:5]=[CH:6][CH:17]=[CH:16][CH:15]=1)[CH3:14])=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11949691Ethyl Indoline-2-carboxylate

Product 1

HCID 68281671HCID 68281671, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

16.6 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and then 10 g of ethyl indoline-2-carboxylate are added to a solution of 12.6 g of o-benzyl-D-lactic acid in 30 ml of DMF and 10.6 ml of pyridine. The reaction medium is stirred at ambient temperature for 18 hours. The reaction medium is concentrated under reduced pressure to ⅔ of the volume of the reaction medium. Ethyl acetate and water are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica cartridge: eluent: gradient: heptane/ethyl acetate from 100/0 to 80/20, so as to give 7.24 g of 1-((R)-2-benzyloxypropionyl)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester: diastereoisomer A, the characteristics of which are the following:

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. additionEthyl acetate and water are added
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified on a silica cartridge

Sources & evidence

ORD record
ord-84cca933806941bc91c400592c743431
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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