2-Aminopropanol → HCID 178472009, compound

HRID 981275Notes

Reaction equation

HRID 981275 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:28]([F:29])=[CH:27][C:18]([C:19]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:20])=[C:17]([F:30])[C:16]=2[F:31])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32]OC(OC)N(C)C.[CH3:40][CH:41]([NH2:44])[CH2:42][OH:43]>C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:28]([F:29])=[CH:27][C:18]([C:19]([C:21](=[CH:32][NH:44][CH:41]([CH3:40])[CH2:42][OH:43])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:20])=[C:17]([F:30])[C:16]=2[F:31])[CH2:13][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 51262-AminopropanolHCID 78373Dimethylformamide dimethyl acetalHCID 10388243HCID 10388243, compound

Product 1

HCID 178472009HCID 178472009, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

In 30 ml of benzene was dissolved 3.00 g of ethyl 4-(1-benzyloxycarbonylaminocyclopropyl)- 2,3,5-trifluorobenzoylacetate. To the resulting solution was added 3.69 g of N,N-dimethylformamide-dimethylacetal. The resulting mixture was refluxed for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue obtained was dissolved in 15 ml of toluene. To the resulting solution was added 518 mg of DL-2-amino-1-propanol. The resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=5/1) to obtain 3.09 g (yield: 86.1%) of ethyl 2-[4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5trifluorobenzoyl]-3-(2-hydroxy-1-methylethylamino)acrylate.

Workup

  1. temperatureThe resulting mixture was refluxed for 30 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue obtained
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by a column chromatography (eluant: toluene/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-2f06640ab56a4a848cbe8f73120f6e42
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

Loading…