Triethylamine → HCID 58655531, compound

HRID 1348602Notes

Reaction equation

HRID 1348602 reaction equation
[CH3:1][C@@H:2]1[C@H:8]([NH:9][C:10](=[O:14])[C@@H:11]([OH:13])[CH3:12])[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[O:3]1.C(N(CC)CC)C.Cl[C:29](OC1C=CC([N+]([O-])=O)=CC=1)=[O:30].[F:41][C:42]([F:49])([C:45]([F:48])([F:47])[F:46])[CH2:43][NH2:44]>C1(C)C=CC=CC=1>[CH3:1][C@@H:2]1[C@H:8]([NH:9][C:10]([C@@H:11]([O:13][C:29](=[O:30])[NH:44][CH2:43][C:42]([F:49])([F:41])[C:45]([F:48])([F:47])[F:46])[CH3:12])=[O:14])[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 790022,2,3,3,3-PentafluoropropylamineHCID 821294-Nitrophenyl chloroformateHCID 21091545HCID 21091545, compound

Product 1

HCID 58655531HCID 58655531, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In an inert atmosphere and under exclusion of moisture, a solution of 95 mg (0.34 mmol) of (S)—N-((6R,7S)-6,9-dimethyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-2-hydroxy-propionamide in 1 ml of toluene was treated with 0.57 ml (0.41 mmol) of triethylamine and 70.9 mg (0.34 mmol) of 4-nitrophenyl chloroformate at room temperature. After stirring at room temperature during the weekend, 0.374 ml (0.34 mmol) of 2,2,3,3,3-pentafluoropropylamine were added and stirring was continued overnight. The solvent was removed by distillation and the crude product was chromatographed on silica gel using a gradient of a 1:3- to 3:1-mixture of ethyl acetate and heptane as the eluent. There were obtained 28 mg (18% of theory) of the title compound as a colourless oil, MS m/e (%): 454.4 (M+H+, 100).

Workup

  1. additionwere added
  2. customThe solvent was removed by distillation
  3. customthe crude product was chromatographed on silica gel using a gradient of a 1:3- to 3

Sources & evidence

ORD record
ord-1a1f84bd278340099578aae68179f065
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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