Dichloromethane → HCID 20716559, compound

HRID 1249920Notes

Reaction equation

HRID 1249920 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:14](=[O:26])[C@@H:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH3:17])=O.[CH3:27][S:28][CH2:29][CH2:30][NH2:31].ClCCl>CO.C(OCC)C>[CH3:27][S:28][CH2:29][CH2:30][NH:31][C:3]([C@@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:14](=[O:26])[C@@H:15]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:16][CH3:17])=[O:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 87697(2-(Methylthio)ethyl)amineHCID 21344952HCID 21344952, compound

Product 1

HCID 20716559HCID 20716559, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(N-t-butoxycarbonyl-2(S)-aminobutyryl)-indoline-2(S)-carboxylic acid methyl ester (0.5 g, 1.4 mmol) in methanol (2 ml), was added 2-methylthioethylamine (3 ml) under nitrogen, and the resulting solution was stirred at 60° C. for 48 hours. The solution was poured into dichloromethane (20 ml), and washed with 1M potassium hydrogen sulphate, the aqueous layer was extracted with dichloromethane (3×15 ml). The combined organic layers were dried over Na2SO4, and then the solvent was evaporated. A white solid was obtained after column chromatography on silica gel using diethyl ether as eluent.

Workup

  1. washwashed with 1M potassium hydrogen sulphate
  2. extractionthe aqueous layer was extracted with dichloromethane (3×15 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent was evaporated
  5. customA white solid was obtained after column chromatography on silica gel

Sources & evidence

ORD record
ord-d285dfd85d1249d6bc58a92033a231de
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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