Ethylmorpholine → HCID 11602781, compound

HRID 2185666Notes

Reaction equation

HRID 2185666 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C@H:12]1[C:20](O)=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[CH2:39]([NH2:43])[CH2:40][CH2:41][CH3:42]>O1CCCC1.C(Cl)Cl>[CH2:39]([NH:43][C:20]([C@@H:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[O:21])[CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 8007ButylamineHCID 62365Isobutyl chloroformateHCID 6932064HCID 6932064, compound

Product 1

HCID 11602781HCID 11602781, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.699 g (25.9 mmol) of N-benzyloxycarbonyl-2(S)-indolinecarboxylic acid prepared as in Example 16 a) are dissolved in tetrahydrofuran (150 ml), under nitrogen. 2.986 g (25.9 mmol) of N-ethylmorpholine are added, at 0° C., followed by 3.54 g (25.9 mmol) of isobutyl chloroformate. After 45 minutes, 1.903 g (25.9 mmol) of n-butylamine are added and the suspension is stirred overnight. Methylene chloride (300 ml) is added and the organic phase is washed with 10% citric acid (3×100 ml) and then NaHCO3 (3×100 ml). After drying and evaporation, a white solid is obtained which is recrystallized from methanol.

Workup

  1. washthe organic phase is washed with 10% citric acid (3×100 ml)
  2. customAfter drying
  3. customevaporation
  4. customa white solid is obtained which
  5. customis recrystallized from methanol

Sources & evidence

ORD record
ord-48e98f551d8b439ead5a462292f7e276
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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