2,4,6-Trimethylpyridine → {3-[N-(4-Benzooxazol-2-yl-phenyl)-N-methyl-carbamoyl]-cyclopentyl}-carbamic acid 9H-fluoren-9-yl-methyl-ester

HRID 1914813Notes

Reaction equation

HRID 1914813 reaction equation
[C:1]([NH:18][C@H:19]1[CH2:23][CH2:22][C@@H:21]([C:24](O)=[O:25])[CH2:20]1)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[C:36]1[CH:41]=[CH:40][C:39]([NH:42][CH3:43])=[CH:38][CH:37]=1.N1C(C)=CC(C)=CC=1C>C(Cl)Cl>[CH:16]1[C:17]2[CH:5]([CH2:4][O:3][C:1](=[O:2])[NH:18][CH:19]3[CH2:23][CH2:22][CH:21]([C:24](=[O:25])[N:42]([C:39]4[CH:40]=[CH:41][C:36]([C:28]5[O:27][C:31]6[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=6[N:29]=5)=[CH:37][CH:38]=4)[CH3:43])[CH2:20]3)[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 401580Benzenamine, 4-(2-benzoxazolyl)-N-methyl-HCID 7006550(1R,3S)-3-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)cyclopentane-1-carboxylic acid

Product 1

HCID 67111395{3-[N-(4-Benzooxazol-2-yl-phenyl)-N-methyl-carbamoyl]-cyclopentyl}-carbamic acid 9H-fluoren-9-yl-methyl-ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

250 mg (0.71 mmol) (−)-(1S,3R)—N-Fmoc-1-Aminocyclopentane-3-carboxylic acid and 0.14 mL (1.07 mmol) 1-chloro-N,N,2-trimethylpropenyldiamine are dissolved in 5 mL DCM and stirred for 2 hours. The resulting product is added to a mixture of 159.6 mg (0.71 mmol) (4-Benzooxazol-2-yl-phenyl)-methyl-amine and 0.14 mL (1.07 mmol) 2,4,6-collidine in 5 mL DCM. The reaction mixture is stirred overnight at RT. The mixture is concentrated under reduced pressure. The residue is taken up in water and extracted with DCM. The organic layer is dried, filtered off and concentrated under reduced pressure. The product is purified by RP-HPLC (water+5-95% acetonitrile (with addition of 0.1% TFA)). The solvent is evaporated.

Workup

  1. stirringThe reaction mixture is stirred overnight at RT
  2. concentrationThe mixture is concentrated under reduced pressure
  3. extractionextracted with DCM
  4. customThe organic layer is dried
  5. filtrationfiltered off
  6. concentrationconcentrated under reduced pressure
  7. customThe product is purified by RP-HPLC (water+5-95% acetonitrile (with addition of 0.1% TFA))
  8. customThe solvent is evaporated

Sources & evidence

ORD record
ord-9da0fa1d89524ea5be2249729f1f7d1d
Source dataset
uspto-grants-2013_12
Patent number
US08614238B2

Reaction notes

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