1,2-Dichloroethane → BOC-Norleucine Amide

HRID 1870305Notes

Reaction equation

HRID 1870305 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][CH2:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.O[N:19]1C2C=CC=CC=2N=N1.C(Cl)CCl>ClCCl>[C:1]([NH:8][C@H:9]([C:14]([NH2:19])=[O:16])[CH2:10][CH2:11][CH2:12][CH3:13])([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 15609364BOC-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 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 to dryness
  5. customtriturated with 20% Na2CO3
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-f99bc27fad2f47fa8b4b789925cec3e2
Source dataset
uspto-grants-2000_08
Patent number
US06096782

Reaction notes

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