Triethylamine → HCID 178472041, compound

HRID 981276Notes

Reaction equation

HRID 981276 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.CO[CH:34](OC)[N:35]([CH3:37])C.Cl.N[S:42][CH2:43]CO.C(N(CC)CC)C>C1C=CC=CC=1.C(O)C>[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:37][NH:35][CH2:34][CH2:43][SH:42])[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

7

Reactant 4

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 10388243HCID 10388243, compoundHCID 20071503HCID 20071503, compound

Product 1

HCID 178472041HCID 178472041, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

In 5 ml of benzene was dissolved 500 mg of ethyl 4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5-trifluorobenzoylacetate. To the resulting solution was added 411 mg of N,N-dimethylformamide-dimethylacetal, and the resulting mixture was refluxed for 40 minutes. The reaction mixture was concentrated under reduced pressure, and the residue obtained was dissolved in 5 ml of ethanol. To the resulting solution were added 157 mg of 2-aminothioethanol hydrochloride and 139 mg of triethylamine, and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=5/1) to obtain 250 mg (yield: 41.7%) of ethyl 2-[4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5-trifluorobenzoyl]-3-(2-mercaptoethylamino)acrylate.

Workup

  1. temperaturethe resulting mixture was refluxed for 40 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-d6c81e89ff914b39af83a0b3cfe84d52
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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