Ammonia → HCID 131717137, compound

HRID 1089835Notes

Reaction equation

HRID 1089835 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H](C(O)=O)CC(C)C)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH3:27]>C1COCC1.O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:14](=[O:15])[C@H:12]([CH2:11][CH:6]([CH3:7])[CH3:5])[NH2:27])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 1549133Fmoc-leucine

Product 1

HCID 131717137HCID 131717137, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride (3.5 g, 10 mmol) in 10 mL of THF was charged with NH3 (29.6% water solution, 1.26 mL, 20 mmol) at room temperature. The reaction mixture was stirred for 30 min., then diluted with 100 mL of water and extracted with ethyl acetate (5×20 mL). The organic layers were combined, extracted with 10% potassium carbonate solution, washed with water, brine, dried and evaporated. Recrystallization of the product from ethanol afforded 1.26 g (36%) of N-(9-fluorenylmethoxycarbonyl)-L-leucine, amide as colorless solid, mp 79°-80° C.

Workup

  1. extractionextracted with ethyl acetate (5×20 mL)
  2. extractionextracted with 10% potassium carbonate solution
  3. washwashed with water, brine
  4. customdried
  5. customevaporated
  6. customRecrystallization of the product from ethanol

Sources & evidence

ORD record
ord-df95c476f7ae452c9a8da660567e362e
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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