1,2-Dichloroethane → N-BOC-Norleucine amide

HRID 1016872Notes

Reaction equation

HRID 1016872 reaction equation
[C:1](N[C@H](C(O)=O)CCCC)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH2:17].O[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=N1.C(Cl)CCl>ClCCl>[C:1]([NH:19][C:23](=[O:17])[C@H:22]([CH2:27][CH2:26][CH2:25][CH3:24])[NH2:21])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 2733747N-tert-Butoxycarbonyl-L-norleucineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 86585124N-BOC-Norleucine amideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 3.47 g (15 mmol) of BOC-norleucine (Bachem), 3.44 g (22.5 mmol) of 1-hydroxybenzotriazole monohydrate and 50 mL of dichloromethane at 0° C. was added 3.45 g (1.2 mmol) of EDC. The resulting mixture was stirred at 0° C. for 1 hour and then ammonia gas was bubbled through the mixture for 10 min. The cooling bath was allowed to warm to room temperature and the mixture stirred for 18 hours. The mixture was evaporated at reduced pressure to dryness, triturated with 20% Na2CO3. The resulting solid was collected by filtration and washed with water to yield 2.69 g (11.7 mmol, 78%) of the title compound.

Workup

  1. customammonia gas was bubbled through the mixture for 10 min
  2. temperatureto warm to room temperature
  3. stirringthe mixture stirred for 18 hours
  4. customThe mixture was evaporated at reduced pressure to dryness
  5. customtriturated with 20% Na2CO3
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-6220f48dd2f745f1a5452a8f992ac2f5
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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