Ethylmorpholine → 1-(n-Benzyloxycarbonyl-2(s)-aminobutyryl)-2(s)-indolinecarboxylic acid n-propylamide

HRID 2185669Notes

Reaction equation

HRID 2185669 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[CH2:34]([NH:37][C:38]([C@@H:40]1[CH2:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[NH:41]1)=[O:39])[CH2:35][CH3:36]>O1CCCC1.C(Cl)Cl>[CH2:34]([NH:37][C:38]([C@@H:40]1[CH2:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[N:41]1[C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:16][CH3:17])=[O:39])[CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acidHCID 602081692(s)-Indolinecarboxylic acid n-propylamide

Product 1

HCID 699686971-(n-Benzyloxycarbonyl-2(s)-aminobutyryl)-2(s)-indolinecarboxylic acid n-propylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.439 g (1.85 mmol) of N-benzyloxycarbonyl-2(S)-aminobutyric acid prepared as in Example 3 a) is dissolved, under nitrogen, in tetrahydrofuran (50 ml) and the solution is cooled in an ice/water bath. 0.213 g (1.85 mmol) of N-ethylmorpholine is added, followed by 0.253 g (1.85 mmol) of isobutyl chloroformate. After 45 minutes, 0.378 g (1.85 mmol) of the compound obtained in step b) is added and stirring is continued for 12 hours. The suspension is poured into CH2Cl2 (100 ml) and the mixture is washed with 10% citric acid (3×100 ml) and then with 5% NaHCO3 (3×100 ml). After drying and evaporation, a white solid is obtained which crystallizes from CCl4.

Workup

  1. temperaturethe solution is cooled in an ice/water bath
  2. waitis continued for 12 hours
  3. washthe mixture is washed with 10% citric acid (3×100 ml)
  4. customAfter drying
  5. customevaporation
  6. customa white solid is obtained which
  7. customcrystallizes from CCl4

Sources & evidence

ORD record
ord-c5c4a5886bd5438d9da99318d783f6ae
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

Loading…