1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → ((S)-1-[2-(6-bromopyridin-2-yl)-2-oxoethylcarbamoyl]ethyl}carbamic acid tert-butyl ester

HRID 1716509Notes

Reaction equation

HRID 1716509 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1)=[O:5].C([C:17]([NH:19][C@H:20]([C:22](O)=[O:23])[CH3:21])=[O:18])(C)(C)C.Cl.CN(C)[CH2:28][CH2:29][CH2:30]N=C=NCC.[OH2:37].ON1C2C=CC=C[C:42]=2N=N1>C(#N)C.O.C(N(CC)CC)C>[C:29]([O:37][C:17](=[O:18])[NH:19][C@H:20]([C:22](=[O:23])[NH:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1)=[O:5])[CH3:21])([CH3:30])([CH3:42])[CH3:28]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 42254381(S)-N-tert-butylcarbonylalanineHCID 534164172-Amino-1-(6-bromopyridin-2-YL)ethanone hydrochloride

Product 1

HCID 86607641((S)-1-[2-(6-bromopyridin-2-yl)-2-oxoethylcarbamoyl]ethyl}carbamic acid tert-butyl esterYield 59.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a suspension of 2-amino-1-(6-bromopyridin-2-yl)ethanone hydrochloride (500 mg, 1.99 mmol) obtained in Step 1 of example 6, (S)-N-tert-butylcarbonylalanine (376 mg, 1.99 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (379 mg, 1.99 mmol), 1-hydroxybenzotriazole monohydrate (305 mg, 1.99 mmol) in acetonitrile (11 ml), a solution of triethylamine (0.7 ml) in acetonitrile (4 ml) was added dropwise while ice-cooled for 15 minutes. After the mixture was stirred at the same temperature for 1 hour, water was added and extracted with ethyl acetate. After the organic layer was washed with water, a saturated brine, dried over magnesium sulfate, the residue obtained by vacuum concentration was purified by flash chromatography on silica gel (n-hexane:ethyl acetate=2:1) and the title compound (456 mg, 59%) was obtained.

Workup

  1. temperaturecooled for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water
  4. dry with materiala saturated brine, dried over magnesium sulfate
  5. customthe residue obtained by vacuum concentration
  6. customwas purified by flash chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-adfa8a424aa74cfcb88b1c6175196bcb
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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